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Me and the Canadian MILF, Part 1 (true story)
It sounds lame, but I met D.J. in an online chat room for New Yorkers. I was in college at the time, bored and horny, and recently broken up with a pretty serious girlfriend. I don't know if it was good or bad luck that caused the back injury that had me laid up in my dorm that week, but unable to walk and bored of TV, I spent a lot of time jumping from chat room to chat room, just bullshitting. I saw D.J.s message in the main chat, asking if anyone was from upstate NY. I checked her profile, and was intrigued by what I saw. A beautiful strawberry blond in her early 30's, with crystal blue eyes and a mischievous smile. I wanted to know more.
At this point, I had been into swinging for awhile. At least as much as a 22-year-old single guy could be. Single men are in low demand, and those that do desire them tend to prefer experience over straight up stamina. Despite having practiced on many a coed, I got more than a few "Sorry, too young" responses in my mailbox. Nevertheless, there were a few couples I had played with, which further developed my affinity for older women. Not that the young, nubile girls I saw daily did nothing for me. But there was something about a woman with half a brain who know what she wanted that turned me on. Call me crazy.
That's precisely what I found in D.J. She said was planning a trip from Canada to the States to visit some family on the eastern sea board. She was going to be passing through my area, and was looking for things to do. I don't know how the conversation turned to sex, but a few hours later, there I was, webcam on and cock in hand, letting her watch me jerk off while she sent me erotic pictures of herself.
I thought she was attractive from the modest face pic I had first seen on her profile, but these only uncreased my lust for her. She was just about everything I pictured an ideal woman to be. My love of older blonds aside, she had curves that I couldn't help but imagine my hands on. She was powerful, yet feminine; the definition of voluptuous.
Her ass was a little piece of heaven, and her tits divine.
I wanted her. I needed her.
Fortunately, I got the impression she felt the same. Over the next couple of days, we met online nightly, showing off for each other. I had always heard that once a woman turns 30, she was constantly ready to fuck, but I had no idea it was like this. D.J. was more than willing and ready to expose her gorgeous naked body to me, play with her tits and get herself off for the camera. I don't know how many orgasms I watched her quiver through. I don't know how many loads I shot watching her. It was clear that there was an attraction that needed to be satisfied. When she told me that she had decided to stop and spend the night with me on her way through, I immediately began to make plans. My back was still out when she told me, but there was no way that I was going to let this MILF get away.
The week leading up to D.J.'s visit went much faster than I had expected it to. My injury healed just in time, perhaps by some miracle, perhaps by dirty talk she and I exchanged on a nightly basis. On the day she was to arrive, I had to work a short shift, so our plan was to meet up in the afternoon and check into a hotel. After I got out of work, we'd find something to do in the city. When she called to tell me that she was outside, my cock jumped with anticipation.
I made my way downstairs, running all the things I wanted to do to her body through my mind. When I got outside, I immediately recognized her black coupe. It helped that it was the only car around with Canadian plates. I hopped in and said hello.
She caressed my cheek with her hand and said, "Wow, I can't believe your a real person." For myself, I was just as much in awe. D.J. was even more beautiful in the flesh, a good 5'6" and proportioned perfectly.
She wore a white blouse, cut low enough to expose just enough of her cleavage to make my cock stiffen considerably. Her denim mini-skirt showed off her toned thighs, and brown mid-calf boots complemented the outfit nicely. She looked fantastic, smiling over at me, and smelled even better.
No matter how good a woman looks, her scent is what really drives me over the top. It was all I could do to keep from taking her right then and there. She seemed to share my urgency.
We shared a passionate kiss and, eager to be off, drove away.
I directed her to the part of town where all the hotels were bunched together. What we failed to realize was that it was only shortly after 1PM, too early to check in. Neither of us minded the wait, though. D.J. and I sat in her car for a good hour, making out like teenagers. Well, I almost still was. Given my past experiences, I was bracing myself for disappointment, but here I was with this gorgeous MILF that I was to bed very shortly. Disappointment did rear its head briefly as my hand roamed her body and found that she was wearing panties. She had teased me that she would leave them off when she came, but my disappointment didn't last long. She was pleasing to the touch, and the eye and the ear, her big tits firm and her ass as well. As I kissed and nibbled and sucked as much sweet flesh as I could, she attacked me with equal fervor. I groped her tits through her blouse, she rubbed my bulging cock through my jeans.
I caressed her inner thighs, she stroked the back of my neck.
I knew that I was in store for a fuck like I had never had before.
I just hoped I could return the favor.
Finally check-in time came, and hurriedly got our keys and went to our room. As soon as the door was shut, I pinned D.J. against it and kissed her deeply. She returned my embrace and let out a moan that made my cock swell. It wasn't long before I had to be to work, but there was more than enough time for D.J. and I to get to know each other a little better.
She helped me undress in a sexy way that only a few women know how to do; running her hands over my chest as she took off my shirt, playfully tugging at a pant leg. When all that remained were my boxer shorts, she took hold of my cock, which was pitching a considerable tent by now. She didn't say a word as she stroked it up and down through the fabric, but the look in her eye conveyed everything. She had thought about this cock more than once and she was just as excited about getting it as I was to give it to her. Without further delay, D.J. slid my shorts off, allowing my 10 inch hard on to spring free. Not missing a beat, she took told of it again and engulfed the head in her mouth. My cock is uncut, so the head is very sensitive, and up until that point, I had never really enjoyed getting head. D.J. changed that in a hurry. She expertly sucked my cock, stroking and bobbing with gusto. Never had a woman blown me so good. What was more, she seemed to be enjoying it just as much as me. My moans of pleasure only increase D.J.'s energy and my hard dick disappeared repeatedly into her willing mouth. I was in heaven.
As amazing as D.J. was at sucking cock, though, I wasn't going to be selfish and settle for a blowjob. Reluctantly, I pulled her up and laid her down on the bed. Laying down next to her, I kissed her passionately while letting my hands roam over her once more. Unable to hold back anymore, I sat up to undress her. I removed her blouse and bra, freeing the tits that I had lusted after. They were an easy D cup, with nipples that were aroused and stiff. I took one in mouth while fondling the other. D.J. moaned and her breathing grew more ragged as I ravaged one, then the other, of her magnificent tits. I couldn't get enough. Sweeter treasures, though, awaited me. Kissing my way between D.J's cleavage and down her stomach, I arrived a the waist of her skirt. Not hesitating, I undid the snap and pulled it off. The sight made me smile. Her panties, which has disappointed me before, had now redeemed themselves.
The front panel of white cotton read "Angel" with a pair of wings on either side. The wetness on the crotch, though, belied D.J.'s true nature. Giving her a little smile, the panties were gone as well, leaving face to face with her amazing pussy.
I had known from the pictures she sent and the webcam shows that D.J. kept herself shaved clean, but seeing the smooth lips glisten with her excitement only whetted my appetite.
I dove into her sweet pussy with abandon, lapping up every bit of wetness I could, only to find it replaced by twice as much. D.J. writhed and moaned as I burrowed my tongue deep inside, then brought it out to flick her protruding clit. Her squirms became more violent when I focused in on her button. As I swirled about it with my tongue then sucked it between my lips, D.J. made the unmistakable sounds of a woman enjoying herself. Her breaths were short and ragged, punctuated with periodic groans of ecstasy. I slid two fingers into her pussy to feel the wetness while I lapped at her clit, and that was all D.J. could stand. Her thighs clamped down like a vise as the orgasm took hold of her body.
Every muscle quivered and she let out a low moan that could only mean one thing. It seemed like forever that my head was trapped while D.J.
came. Finally, she released me, breathing deep with a peaceful look on her face. It was time.
By now, my cock was as big and hard as it had ever been. At least the normal 10 inches, if not a tad bit more. Of course I'd made women climax before, but watching D.J. cum turned me on more than all the rest combined. Despite not fully having caught her breath, D.J. was ready for me, spreading her legs as I made my way back up her body. We shared another kiss as I placed the head of my cock at the entrance of her sopping hole. She was ready, and so was I.
One of my favorite things about sex is the look on a woman's face when I enter her for the first time. While I may not have an all-time huge cock, my 10 inches is a lot more than most women are used to. The wide-eyed look of, "Oh my God, I didn't realize how big this thing was until it was inside me, " never fails to satisfy me. D.J. was no different. I could tell she began to feel it when I first began, fucking her slowly with the cockhead, plunging a little bit more inside with each stroke. Her wetness allowed me easy access, despite my size. By the time I was buried deep in her pussy, my balls touching her ass, D.J.'s mouth hung open, though no sound emerged. Her eyes rolled a little before she shut them and tossed her head back in ecstasy. I wanted to make sure she felt every inch, so I began to slide my cock in and out slowly. As slow as I went, though, her breath didn't do the same. As D.J. panted her excitement, it only served to increase my own. It wasn't long before I was pounding her gripping, spasming cunt with all the force I could muster. D.J. looked like a woman lost. I sat up on my knees and pushed hers toward her chest, to allow myself deeper penetration. D.J. had her hands on her head and a look like she couldn't believe what was happening, while her big tits jiggled and danced with every thrust of my cock. "I think I'm going to have to start changing my expectations in life, " she managed to get out in between gasps. I don't think either of us know how many times D.J. came, but by the end, her body was spent, a quivering, heaving mass. I had yet to cum, but D.J. had a special plan to me.
Gathering herself, D.J. moved me to sit on the edge of the bed. Once I was in place, she got on her knees and took my stiff cock in her mouth once again. Where the first blow job had been aggressive and passionate, this one was slow and sensual.
She didn't want to make me cum. She only wanted to please me. She was doing a hell of a job. After several minutes of this exquisite treatement, D.J. looked up at me, then laid down on the bed. Both of us knew that we didn't have time to fuck again. I had told her, though, how much I love to cum on a woman's chest. I can't think of a place I'd rather shoot my load than on a nice, big, round set of tits.
I approached her hesitantly at first, but mounted her chest with enthusiasm when it became clear that's what she wanted too. D.J. pushed her fabulous globes together, creating a deep channel in her cleavage. My cock was still slick for her mouth, so I eagerly slid it in between them.
The smooth skin of her tits felt just as good as her expert mouth and her warm, wet pussy. I placed my hands on hers, pushing them tighter around my cock, flicking her nipples with my thumbs as I shuttled it back and forth. Whenever the head came within range of her mouth, D.J. made sure to give it a quick lick or a suck that drove me crazy. Soon, I couldn't hold back any longer. I slid my pulsating cock from between D.J.'s tits, gave it a couple quick strokes, and shot an enormous load with a groan of ecstasy.
The first spurt flew clear over her head onto the headboard.
The rest were better aimed, covering her chest and neck in sticky goo. It was a perfect cum shot.
Leaning back to catch my own breath, I noticed a bit of spunk had found it's way into D.J.'s hair. When I pointed it out, she laughed and said, "What would my mother say if she knew that an hour after I met a guy, I had his cum in my hair?". This light mood carried us as we cleaned up and dressed. On the way to my job, D.J. and I made a plan for her to pick up later, and I gave her some ideas on what we might do that night. When she dropped me off, I was already thinking about the evening's festivities.
That'll be for next time.