impossible/ unexpected sexual encounters or relationship?

[vannessangelia]

Anyone has had a relationship or had sex with someone that u have never expected ...ever?

that was unexpected and u always find it impossible....yet u finally did it...

like u are a shy, average looking guy neva chat up with a girl....but u end up hooking up a hottie?

or hook up with someone's boyfriend/girlfreind/ partners?

[doitallthetime]

There was an older married lady I was chatting with online years ago, she was 44, I was 21. We got to be pretty friendly and eventually she got me a job working at the place she was employed. We never even met nor saw each other until I was in the office filling out the application and she walked in for work. She took one look, quickly averted her eyes and carried on. Initially, I thought it kind of strange, but brushed it off and assumed she was just running late.

Time passes, we still work there together and we've been carpooling for awhile since we lived real close to each other...still friendly, nothing out of the ordinary. Had great conversations on the rides to and from work, even brushing on sexual topics, and overall got to know each other pretty well. One night on the drive home, we got into a healthy discussion on sexual preferences, and I got pretty aroused. Little did I know, she did too, and in the middle of talking she reached over and started working my cock through my pants. It felt great, and once I got over the initial shock of what was going on, I got highly aroused, and the more uncomfortable it became to keep it my hard dick in it's prison. I worked up the courage to ask her if she wanted to touch it, and she readily obliged and undid my belt and zipper, readily taking my rock hard dick in her hands.

On the first couple strokes, there was a massive amount of pre-cum that had already leaked onto my boxers, but there was far more that had built up that came spilling out of my head and onto her hand like a river. This did something to her, and she gave me a few more strokes to get it shaft lubed up with precum, got one large dollop on the head of my cock, and then in one fell swoop, took my entire shaft in her mouth, clear down to my balls, pulled her head back up and and began to give me the best cocksucking I had ever had at that point in my life. While she pleasured me, it's like she wanted to taste me, as she would occasionally stop and work her fingers along the bottom of my shaft to the top in order to coax more precum out, which as horny as I was, came out in steady supply. She would let it come out, start dripping down the head and methodically lap it up with her toungue, then proceed to suck dick. With this turn of events, I was in a position now to have better access to her tits and twat, and eagerly cupped her tiny tits, noticing that while they were small, they were a handfull still quite firm, even after 4 kids. I continued to play those small, teenage size tits if hers and began to work down to her hole, and I found a pussy that was amazingly hot and wet and easily took all 4 of my fingers with ease.

At this point, I had never cum from a blowjob, so I knew her efforts would be in vain. But she was a trooper, and sucked and slurped my dick the entire 45 minutes of the drive back to my parents house. I tried so hard to fuck her once we parked, but it didn't work out. I was force to go home, and went straight to the bathroom to finish the job. It took all of 30 seconds of jerking off to blow 5 full ropes of cum, and that act was repeated a couple more times during the night with the memory fresh in my mind.

The next day, we rode into work like normal, did our shift and began the drive home. We didn't really bring up the events of the previous night, but exchanged a couple of knowing glances at each other, and I could tell she was flusterd, and so was I. I got an idea to feign car trouble, and made the car jerk a little using the gas pedal. This seemed to worry her, and I suggested we get off the highway and at least have a look under the hood. I pulled into a quiet industrial area just off the highway with decent lighting, popped the hood and we peered into the engine bay looking for anything out of order.

This gave me a straight shot of the view down her shirt and almost instantly gave me a hard on. Without thinking, I went behind her and thrust my hands up her shirt and started pawing, squeezing and working those small tits of hers in an attempt to get her worked up. She let out a small gasp of surprise, that quickly turned into that familiar "ohhhh my god, mmmm". I pulled her blouse up and took the closet nipple in my mouth, this really got her started, and she moved her hands back and expertly got into my pants, freed my cock and began to stroke it.

I decided that this was it, I was going to attempt to fuck this MILF and would succeed this time. After playing with her tits for another 30 seconds to get my point across and get her worked up, I moved to her side to she could see my dick and continue to work it, this also gave her the option to suck it again if she wanted, and I took my left hand and stuffed it up her dress. To my surprise, there were no panties to in the way, and my fingers found that same cunt was soaking wet like the night before. I put two and two together, and relized there was no way she got that wet so fast. I tested again and verifed that I could still fit all 4 fingers up in her cunt with room to spare...my fingers lubed up, I went straight for her clit, stroking and rubbing that nub. While I was playing with it, she lustfully and in between heavy breaths, confessed to me she had been dripping wet since she woke up that morning, had masturbated several times before work, and while at work, had made herself cum 3 times in the bathroom, after letting me know this, she seemed releived and took my cock in her mouth again and began to suck like a pro, just like the night before.

I let her continue for about a minute, pried my cock away and told her "we should probably get going". She reluctantly agreed and as she raised her arms up to grab the hood of the car to close it, I "helped" her from behind getting the hood down. When the hood slammed closed, this put her in the perfect position and I went into action and I put a hand in between her shoulder blades, and pulled her dress up high enough, let go and grabbed the shaft of my cock and slid that fucker balls deep into her pussy, all in the span of one second.

She yet again left out a gasp of surprise and "oh my god, he did it" and from there, things fell right into place. She was letting me do to her the things she had imagined and masturbated to earlier that day and was geting exactly what she desired...to be completely and utterly fucked senseless by a younger guy. I buried every bit of my meat in her and did so for about 5 minutes and stopped as things were heating up after seeing a police car pass close by. I didn't really notice, but in that short span where we gave into our desires to please each other, it got real warm and sloppy wet. I didn't pay much attention or give it a lot of thought, just figuring she was very excited. I knew my pants and her dress were wet. What I didn't know it at the time, but this middle age married woman was a squirter!

Right as we got into the car, she took her position continued to stroke, suck and pleasure my cock for the rest of the drive home. Once we got near my place, I pulled into a church parking lot. As I began to pull into the parking space, I told her to stop sucking me off, hike up her dress, spread her legs and get that pussy ready and in position. With a giggle, she eagerly complied, and no sooner did I put the car in park, I quickly moved over and rammed my hard and ready tool into her, intent of destroying that pussy. I was so eager to fuck this older willing slut, that I didn't even turn the car off until I had resumed fucking her.

We fucked, and fucked and fucked again for about 3 hours, mostly missonary, but the angle we were screwing at made it possible for me to ram my cock into her whenever she demanded me to. After we started going at it again, she came rather quickly and with the position we were in, I could feel and see the liquid gush from her pussy. Unfortunatly, she was very embarrased, she had a very strong orgasm, and wasn't able to keep the squirting at bay. I don't think she really knew herself what was happening, but she kept assuring me she hadn't pissed on me. I did a smell check just to be sure, and told her not to worry, and made her promise not to hold back when she was going to cum again, and resumed pleasuring her with my eager and willing penis.

With this freedom, when this woman came, she CAME. Her next three orgasms were without question just as or more intense, as I could tell from her quivering and the fact that she was squirting rivers of her hot sex juice, and had completely drenching the bench seat of her car. The latter ones had her damn near screaming with pleasure, but much less squirting.

For me, I shit you not, I came three times in a row that night and never stopped pounding my dick into her. One of the hottest moments was when I was about to blow for the first time, let her know, and began to pull out to shoot my load. She promptly let me know this was unacceptable and ordered me to shoot my loads inside her, and then got her legs around my waist and force me to do it her way. I started to protest, but she told me, and I quote "shut up and fuck me. I'm fixed, and you better not stop...you let me cum on you, and now your gonna cum in me so I can feel it shoot up in me". And so...I did.

That was the beginning of years of fucking for us....I've banged her anywhere from a public storage place, a parking garage, our bosses desk at work during the middle of the day (closed in room with a door thankfully), our office conference table (we almost got caught) the stairways at work. Going out for lunch was code for us..we would drive to a secluded spot and I would proceed to make a meal of her twat. Making her cum with my mouth was awesome, there is nothing like a woman squirting in your mouth, the taste is unlike anything.

Our most daring feat was conceived by her one night as we drove home from work. She instructed me to go to her house. We went inside and she lead me into a back room. Here in this room was her husband, passed out drunk and snoring away. I was nervous, but she pulled out my limp pecker and worked that thing hard in no time. Once I was hard and ready, she sat me down on a stool, turned her ass to me and rode my dick right in front of her husband. Once I got close to popping, I let her know, and she hopped of my cock and orderd me to jerk off into her mouth, swallowed my load, and told her husband how good it tasted! This was by far the most risky thing I had ever done, but it was exciting as hell. I was in awe and immediatly aroused all over again. I pulled he into her living room just down the hall and proceeded to eat her out with enthuasim, she of course came, squirting all over the couch, making a wet spot that smelld of her.

This woman also took it upon herself to be the first to make me cum from a blowjob, and she did it, working for well over an hour and the end result was one massive and stong ejaculaton in her mouth, which she took every drop with a smile, declaring it her reward for the effort. Any woman since who has managed to make me cum by sucking me off, they think it's skill, but it's not. I let them try and do their thing, if they're good I let them go to town, after awhile I shift my thoughts to this cocksucking queen and imagine it's her sucking my rod, and before you know it, I'm firing off a heavy load of jizz into some other girls mouth.

(the following is another escapade, which I have to bring up and tell. That's how hot it was)

As time went on, we eventually moved to different areas, but still keep in touch, and I visit her when I can (yes, she is that good of a fuck). This time, I got a ride up and had arranged for my girlfriend at the time to pick me up from her place. Before walking out the door, I hugged my MILF goodbye and quickly wispered after I left to strip and be waiting on her knees in the kitchen, with her hands cupping her tits and pinching her nipples, and to have her mouth open, and she was not to speak a word.

Of course not too long after we left, I managed to discover i had "forgotten" my wallet. When I returned to retrieve my item I kissed my current girlfriend and did a playful fondle and squeeze of her big tits and told her I'd be back in just a minute. The walk to the house door gave a rush of anticipation and with each step, my dick woke up stood at attention, solid and firm. Once back inside, I saw she was waiting as instructed and as I walked over, I undid my pants and produced my hard and ready member and stuffed it in her hot wet mouth. Gently grabbing a handful of hair on the back of her head, I guided her mouth to do what felt good to me. It got to a point where I was really into it forgot about the no talking thing and let her know she my personal slut, firmly telling her she that "you're cunt belong to me and this dick is going fuck it whenver and where ever it wants". This got her even more turned on, and she hurried the pace of her dick sucking and eagerly gobbled, slurped and took all all 7 inches by mouth and still managing to lick my balls.

This was hot as hell, but not enough, I knew time was limited and I needed to finish quickly and empty my balls in her, so I bent her over the sink, where we both had a view of my waiting girlfriend in the car. I plunged my dick inside that sopping wet pussy and began to move in...out....in....out....balls deep every time and hitting her cervix, reaching around and rubbing her clit at the same time. I told her to look out the window at my girlfriend in the car, and continued to pound her pussy. While fucking her, I assured her that she, as my slut and my cumdumpster....her pussy and mouth are the best an never compare to any other woman I fuck, . We contined on, lustfully pleasing each other, keeping quiet except for a few moans and groans, we startied to become lost in out act...and we took a little too long. As involved as we were with pleasing each other, we got a little TOO involved with it and didn't notice my girl had grown impaitient, had gotten out of the car and was walking towards the house, the sound of the car door shutting alerted us. Once noticed, I let out an "oh shit", my MILF saw her coming toward us moaned "don't stop you fucker, don't stop".

I thrust in and out that cunt a few more time noticing that she was watching my approaching girfriend, my nervous energy was making each motion quicker and more forceful than the last in an attempt to quicken the act of filling her pussy with my seed, and in about 10 pumps, she let out a stifled shriek of pleasure and squirted her hot wetness all over my cock. The next few thrusts from there made a very sloppy wet sound. This sound and wetness assured me that I had gotten her off, and the continued approach of my girlfriend raised the intensity and promptly sent me over the edge. I came with such force, she later told me she felt the first 3 shots hit her cervix and that the amount that I had left in there was huge.

My job done and my balls emptied, there was no time to clean up, I pulled my rod from her cunt, she flipped arund and took my entire member down her gullet one last time, then she bolted to her room, ass jiggling and those tiny tits barely moving, commenting on the way that she could taste her pussy and my cum mixed together..and it was wonderful. I quickly stuffed my still hard dick into my pants, zipped up and met her at the door with my found wallet, hoping the smell of sex would not reach her nose. It didn't, and the whole ride home, I could feel the wetness and occasionally catch the scent of her pussy wafting from my crotch. I would occasionally discreetly smell the fingers I had used to work her clit. That smell would kept me semi-hard the whole ride home.

On the drive back I started the process of getting the idea of sex in my girlfriends head with and a little playful tit fondling and leg rubbing, gradually ending up grinding rubbing her crotch, and we when arrived home 3 hours later, she was wet, horny ready, and with a smile, I was fucking the girl that came so close to seeing my fucking my MILF. I really did take pride in giving the dick to girlfriend, knowing that i was mixing her pussy juice and scent with that of cunt of the MLF who I had fucked earlier. The one whose cunt I fucked good enough to make it squirt all over my shaft. That thought led to some pretty hot fucking, and that night she actually let me shoot my load all over her tits for the first time (mmmm...38D perfect, natural tits on a 42 year old, who was a bit of a prude and borderline boring in bed....but those tits....) I was hoping to do some pussy to mouth to in effect have her unwittingly taste and take in pheromones from the other pussy I had fucked with my cock earlier...but it didn't work out. However, knowing that I was able to combine the scent and secretions of that hot squirting pussy still left on me with the pussy secretions of the girl I was fucking on a regular basis was good enough and gave me lots of things to think about.

No matter who I'm with or who she is with, we still stay in touch and make time for each other and still fuck the shit out of each other every chance we get, even if it's for a quickie in a back alley on her way home from work. This woman has a special place for me and will always be in my memory. I even keep a saved voice mail from long ago and listen from time to time. Just hearing her voice to this day still get's me rock hard in no time flat, and every time without fail, a supercharged batch of semen rockets from the head of my cock, always landing on my chest, sometimes as far as my chin, and this is blowing my load from a seated position...which lends more credit to the power of this woman.

[Alfred]

Incredible story! Thanks for that...
I want a MILF like that!

[master 1955]

WOW !!! i would love to find a MILF in my area. I hope there is one on line now.

[doitallthetime]

Thanks...all that was totally real, no way could ever make that kind of crap up.

Think I may post a story about two roommates I had a tryst with here soon, hot as all hell, but ended with drama unfortunately

Yeah, I'm kinda a man whore...

[Balcode]

I perhaps shall keep silent, you've covered almost anything, haven't yah?

[doitallthetime]

Meh, no. Just a free spirit who has had some fun times.