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Wendy Fantasy

Several years ago some of my friends and I would meet up with another friend to go to an area near his mother’s home with the purpose of hunting deer, rabbit, and squirrel. During one of our many trips up to that area, he introduced us to his sister, Wendy, and her family, as they were out visiting their mother.

Over the many years that I have known this woman, an attractive woman to which whom I have had numerous fantasies that have found me getting into her panties one way or another. Almost from the first time that I was introduced to her by her brother, I started having these thoughts and dreams (usually wet ones of course) of her and I fucking each other’s brains out.

Let me briefly describe this attractive woman. At the time; she was a good looking woman standing about 5 foot 5 inches, I would estimate that she weighed in at the time of this story at about 145-150 pounds, had light brown hair, and tanned skinned. I would further guesstimate that her measurements would be on the 37B-26-36 side of things. In other words, she was, and still is today, a very fuckable looking woman.

Most times when Wendy did not wear some sort of a jacket or coat, I could also see that she usually wasn’t into wearing a bra. Occasionally her tits would sway back and forth under her blouse/shirt when she moved around or laughed. From time to time her nipples would present themselves by standing erect against her top, as if she was saying, ‘Come on over here and suck on these for a while.’ Every now and then when the top she was wearing had a loose-fitting collar, she would bend forward, thus allowing the top to fall open and away from her tits, putting the top of them and her extended pinkish brown areoles and nipples on display.

Shortly after the first time I had been introduced to Wendy; her husband (Steve), their children (Denise, Gerald, and Paul (the later whom she was pregnant with shortly after our introduction)), and her, were in a wooded area near her mother’s to cut down/up a few oak trees to use during the forthcoming fall and winter in their fireplace. I was in the area on one of our hunting group’s scouting trips for the approaching deer season. I stopped by the spot where Wendy and her family were at, to take a break and to talk a bit with them, especially with Wendy.

Steve was using a chainsaw in order to fall a couple of oak trees, cutting them up, and then using an axe he had with him, he would stop dropping trees periodically to split some of the 18-24” sections cut, so that he could load them on to his pick-up to take to their home, and to Wendy’s mother’s home. At one point, while Steve was cutting up some sections, I picked up the axe and started helping out by splitting some of the wood chunks, and then stacking the pieces in their pick-up.

One chunk of oak that Steve had cut out was a pretty good sized one. It did not want to split no matter where he or I hit it. Steve commented that he would just leave it for later. I said “No I’ll get it into your truck. That way, you can take it to your house to put in the fireplace whole some cold morning.”

Wendy said “The size of that, you will never get it into the truck.”

I took that as a challenge and asked her “What will you do if I get it into the truck?”

She commented “You’ll never get it in there, but what would you like, if you do?”

I just winked at her and said something like “You’ll probably never really know, now do you?”

Steve, off to the side, laughed at our comments. I am sure that he knew, that in the back of my mind, I found his wife attractive, moreover that I would like to get access to the braless tits that she had on display under her top that day, and furthermore that I wouldn’t mind getting in her panties to lick her pussy to at least one orgasm, if not more, as well as to fuck her senseless to multiple orgasms.

From that day forward, I thought, and fantasized about, what it would be like to get with Wendy, in order to fuck her. I would often wonder, ‘Would Steve be willing to share her with me? And if so, would she be a wild fuck? Would she be willing to suck my sock? Would she take my cock down into her throat and swallow the creamy jiz released from it? Would she and I become regular Friends With Benefits? Would we be able to meet whenever and wherever we could, to get naked together in order to fuck one another?’

Over the years I have numerously wondered, ‘Does Wendy keep her pussy au natural, trimmed, or is it completely shaved clean? Does she have any nipple or clit piercings? If she does have them, are some of the rings attached to each other in order for her to enhance any of her sexual pleasures?’

In my dreams I have pictured her/us in all sorts of ways. The two of us have met in motel rooms. We would then find ourselves stripping each other naked almost before the door would be completely closed. Occasionally after we would be naked, Wendy would get on the bed on her knees in order for me to enter her from behind doggy style without any preliminaries at all. We would just fuck the daylights out of each other, in all sorts of positions, for a couple of hours, for no other purpose than for unadulterated sex.

More than a few times I have fantasized our time together being in a motel room where we would take our time and enjoy each other’s bodies for hours on end. Both of us licking, kissing, and caressing the other all over. During these types of meetings I could see myself starting our sessions by kissing and licking down her legs to her feet. Once I would get there, I would lick each of them completely; soles, sides, instep, and across the tops. After a while I would take each of her toes in my mouth and suck on them one at a time.

On other times, I have further fantasized the two of us taking our time and making sweet love to each other. Both of us taking our time, kissing and caressing each other from head to foot, and back again. Then we would move on down the other’s body to spend several minutes paying attention to their nipples. We nibble, lick, suck, kiss, and tug on each in turn. The nipple not receiving any oral attention meanwhile, would be getting attention by our finger playing with it, twisting, pulling, and squeezing it.

Slowly our mouths/tongues would work down over the other’s belly to their bellybutton, which would get a thorough licking, before we would continue moving down to the crotch of the other to lick, kiss, suckle, nibble, tongue flick the other’s cunt/cock. She would sometimes swallow my cock on down in to her throat, and I would bury my tongue as deep as I could get it in her pussy.

The later would of course eventually find us in a 69 position satisfying each other. Her swallowing my cock down, then dragging her teeth across my cock as she slowly rises back off of it. Then she would alternate that with nibbling/licking along the sides of my cock, moving up and down on it. Meanwhile I would have my mouth over her pussy, nibbling on her pussy lips and clit, then dipping my curled tongue as deep as it can get into her pussy and flicking it on her clit from the underside.

Ultimately we would move in to a missionary position, allowing for my cock enter her soaking pussy. She would put her legs up over my shoulders and we would pump against each other in alternating speeds. Slowly at first, moving on to a faster pace, back to a slow in and out pace. She would in time start to moan louder and louder, whereupon I would pick up my pace and drive in and out of her as fast, as deep, and as hard as I could.

When I could feel that she was about to have an orgasm, I would move her legs off my shoulders, slow the pace down to a slow in, and even slower withdrawal out, of her pussy. Continuing at that slower pace for a few minutes, then I would again begin to pick the pace, back up to driving my cock hard and fast, in and out of her soaked pussy, until she screams out in ecstasy, clamping her legs around my body, holding my cock inside of her, and her pussy tightening and releasing my cock in its warm sleeve. We would both scream out in our mutual orgasms as we peaked out and cum simultaneously.

As we calmed down from our earth shattering cum, we would lay side-by-side caressing each other. Running our fingers and hands over each other, lightly kissing each other. Sometimes, we would make love a few more times, and sometimes one or both of us had other things to accomplish, so we had to cleanup each other and get dressed to leave from our sexual interlude.

However, my most dreamt about fantasy involving Wendy, is that after some of our sexual interludes, I would start to lick and kiss her anal opening while we would be in a 69 position. I am sure that Wendy would probably jump upon my tongue touching her ass, as I would venture to say it would be totally new experience for her.

Ultimately I would lick and kiss from her pussy down to her ass and then back up and over her pussy. I would continue that for a several minutes before I would attempt to push the tip of one of my fingers into her anal opening. I am sure she would jump some more upon my attempting that. I would tell her “Lay back and relax Babe.”

She would most likely say something like “I have a virgin ass. I don’t know if I can handle my ass being penetrated by your fingers. I have never had my ass played with before, let alone been penetrated by a finger, or a cock, and I feel that you really want to put your fantastic cock in my ass. I am not sure I can take that.”

I tell her, “Enjoy a journey into a new sexual pleasure for you. I will take my time getting your rear opening prepared for these new pleasures, by using my tongue and finger, eventually my fingers, especially before I would ever attempt to put my cock to enter your beautiful ass. Don’t worry though Sweetie, if you say stop, I will stop. However, I think if you give it, and me, a fair chance, by using my tongue and fingers to get your ass ready, ready for an eventual penetration of it by my cock; that you will enjoy being fucked back there.”

She then coos, “OK let’s see how it goes. You have always been gentle with me throughout the times that we have known each other, during all the other things that we have done together before, and especially during all of our sexual interludes. I do believe that you will be gentle with me, while you are introducing me to a new facet of our sex together.”

As I continue kissing, licking, and nibbling in and around her pussy, and the kissing and licking of her anal rose bud, I slowly begin to massage her anal opening with one finger. Moving that finger leisurely around her ass, and slightly inserting it now and then. After a few minutes, I slowly insert it into her and begin to move it around inside of her rectum.

Following these ministrations, and when I feel her ass relax a bit, I move to insert a second finger into her ass. Flinching slightly, she relaxes yet again as I tell her “Easy Wendy, I am just trying to stretch it out a bit, to see if I can get your rear ready for a third finger inside of it.”

Moving my two fingers in and out, I alternate the angle of their approach in to her ass, slowly twisting them around. In doing this, her sphincter opening relaxes some more. It is showing me that she is beginning to really enjoy having my fingers in her ass. She begins moaning more and more with each movement of my fingers.

A few more minutes, and I introduce a third finger to her anal entrance. Wendy flinches some, ever so slightly this time, less than the previous times when my first and second fingers entered her. Wendy relaxes fairly quickly and begins to move her body with my hand pumping in and out of her.

Moving my mouth down a bit, I use my tongue around my fingers and her ass. Every now and then I remove my fingers, and insert the tip of my tongue in to the rim of her ass, blowing slightly while doing so. Her moans seem to get louder as I continue tonguing her ass. In time I push my tongue deeper inside her ass.

Slowly, I reinsert my fingers into her, moving them in and out. When I feel her ass loosening up some more, I insert a forth finger into her ass. Wendy flinches again ever so slightly, moaning at the same time “Wow! That feels wonderful! I love what you are doing to my ass with your fingers, and especially with your tongue! I can’t believe I am now taking four of your fingers in my ass. I want to feel your cock in there! I want to feel it pumping in and out! Then I want to feel you cuming and filling my ass with your jiz.”

Moving my hand about, with my fingers in her ass, it starts to stretch out ever so much more. Separating my fingers a bit stretches it out even more. I move my tongue back to her pussy and kiss, lick and nibble on it. The juices that are coming from her pussy, when I am doing these things, are flowing so much that I can hardly swallow them fast enough to keep from drowning.

Wendy squeezes her legs tight against my head and hand as she lets out a loud moan of “I am going to cccccuuuuuuummmmmm! You are making me feel soooooo wonderful! I can’t believe how fantastic I feel with the things you are doing to my body! Please get my ass ready for you to fuck it with your wonderful cock!”

After she comes down from that orgasm, I take my fingers from her ass, flip her over and get her up in a doggie position on her knees. Moving between her legs behind her, I slowly insert my cock into her soaking wet pussy, and pump it in and out a few times while I play with her rear opening.

Pulling my now soaking wet cock out of her pussy, I place it lengthwise over her ass and move it up and down. I ask her “Where would you like for me to put my cock now babe? Back in your pussy some more? Or would you like to find out what it would feel like in that virgin ass of yours?”

Shakily Wendy says, “Please put it in my ass! You have me all worked up and I want to feel what it is like to have it pumping in and out of my ass. I want to feel your cum inside my ass! Now! Please put it in my ass now!”

I put my cock back into her pussy to get some more of her juices on it. Then I pull it out and aim my cock head at her rear opening. Slowly I move my hips forward, pushing the head of my cock against her sphincter while I tell her “You will need to relax sweetie so my cock can enter your ass. I will take it slow and easy so you can get adjusted to it. It will hurt a bit while my cock enters you and when I get my cock fully inside for a short bit. Much like your pussy did when you had your first cock in it and lost your vaginal virginity. Let me know if it begins to hurt more than you can tolerate though. I will pause to see if you can adjust to it and begin to enjoy a new pleasure center, or completely stop if that is what you want.”

While I am telling her that, I push forward, my cock head slides through her sphincter, on in to her rectum. She tenses up a bit, and I stop. I whisper to her “Relax sweetie. I will stay still right here for a bit so you can get used to my cock’s presence. Your ass will be able adjust to it shortly.”

When I feel her sphincter muscle loosen a bit, I slowly push a bit more of my cock into her, again stopping after about an inch. A few minutes go by and I can feel her muscles loosening some more, so I push a bit more in to her. This goes on a few more times, to where my cock eventually is fully inserted inside her ass.

My pubic hairs are now touching Wendy’s gorgeous ass, an ass that I have been dreaming about, for what seems like forever. An ass that I have wanted to fuck since the first time I laid my eyes on it, even though it was encompassed inside a pair of panties and jeans back then.

Slowly I begin to pull my cock out of her ass to the point where the head of it is the only thing still inside of her. Holding there for a few seconds, I slowly start pushing forward again, pushing my cock back into to her until my pubic hairs are again against her beautiful ass. Her muscles seem to loosen up a bit, so I start moving at a faster pace until I am pumping in and out almost as fast as I have done while fucking her pussy.

She begins to push back with every thrust of mine forward. Wendy begins moaning “That feels wonderful! I never thought that having my ass fucked would feel so great! I am so glad that you wanted to introduce me to this fantastic way of making love! Harder! Faster! Please fuck my ass harder and faster! I want to feel your cum inside my ass!”

I reach around with both hands and begin playing with her pussy, tweaking her clit between my fingertips. She really starts to moan to the point she screams out “I’m ccuuummmiiinngg! Oh this feels so wonderful! I love what you are doing to my pussy and my ass! Thank-you for showing me pleasure that I never knew could exist! Egod I’m ccuuummmiiinngg!!!”

As Wendy cums again, I feel my hot jiz building up in my balls to the point that it begins shooting out of my cock and filling her now welcoming ass. Holding on to her hips, I ram my cock fully in to her ass and keep it buried there until my cock slowly starts to shrink up and it pops out of her ass. When it does I roll off to the side and pull her to me, kissing and caressing her. I ask her “So how was it? For your first time getting your ass tongued, finger played with, a hard cock in your ass. Was it something you might like to repeat?”

She coos “Oh yes! Thank-you so very much for introducing me to this new way of sexual satisfaction! I want for you to play with my ass any time you desire! I will be a bit sore back there for a bit, but overall my ass feels as if has been fantastically fucked! It was a truly new pleasure and was very enjoyable!”

We lay there for several minutes holding each other, lightly kissing each other. We finally decide that it is time that we get cleaned up and see about grabbing something to eat before she has to get back to her home, where Steve is waiting for her to tell him all about her newest and hottest experience of ours.

As I said up front, all of this has been fantasies of mine for several years, which involve a beautiful woman, that I have had the greatest of real non-sexual friendly pleasures of knowing, and moreover purely fantasy sexual pleasures dreaming about.

End of Story