Have you ever had a woman you wanted and lusted over for a long time, and then, when it finally happened, it was all you imagined it would be, only to be disappointed at the end?

We both knew Maya back in hs. She was by far the pretties girl in the entire school, but she wasn't popular, no, she was one of the nerdy girls, yet, the way she dressed, so closed and unrevealing, nor the way she acted, all shy and introverted, couldn't fool guys to look over her hotness.

She was our friend, and we both lusted over her. I tried something, she rejected me, like she rejected everyone - no one could touch her.

Now, this all happened in my home town, and as I went to college, she stayed, with him, my best friend. First Christmas I came back home from college, they already became an item, but we kept contact, all the way through college. Every time I visited, she evolved more and more, into a mesmerizing woman, being with him gave her confidence, both socially, and about the way she dressed, behaved.

I got married to a girl I met in college, in the city, after graduation, and they started living together, back home.

Twenty something years have passed. I got divorced in the mean time, and bought a little condo back home, for vacation, and started spending more time there. We lost touch over the years, but when I met him, and asked him about her, he confessed they broke up years ago. Then I bumped into her...

Saying that a 44 year old is stunning, always has to be taken with a bit of salt, but man, she was. I had no time to waste, texting have started, coffee dates, dinners... After one, she agreed to come back to my condo. When I kissed her, she kissed me back, and then surprised me, by going down on her knees, by herself, moments after, and unbuttoning my pants. When she took it in her mouth, I couldn't believe it. This was a woman, who I have been obsessed with for over two decades. I jerked off to the thought of her, thousands of times, and there she was.

It was wonderful, sensual, romantic. She came, while on top of me, tweeting like a little bird. Then I got to be on top, and when I was about to nut, I pulled out, but my excitement got the better of me, so instead of shooting for her belly, I unloaded all over her bald, perfect pussy.

"You didn't have to,"she commented,"there is no worries there".

That night, I learned that he left her, because she couldn't have kids. I also learned, that she is absolutely still and forever in love with him, and I decided, that that plot, is not healthy for me.

I did buckle, two more times, we spent two more nights together, before I packed my shit and got out of there, not to come back for another two years. She may be my perfect woman, but I am not her perfect man, and that would come back to bite me in the ass, sooner or later.

And that is my, said, love story.

I don't care what anyone says. When jerking off I love either having a plug in my ass or fingering myself. How many guys her like or enjoy doing that to themselves. Makes for an amazing cum shot. And it feels good too

my cousin D. Let's jerk off for her now?

My gf’s sist, am I wrong for jerking to her?? What would you do to her? 

So I have this girl who is me and, my fiancé's friend and, I've known her for years she's like a sister type to me but, she's got huge tits and, kinda frumpy, nice ass and, so everytime I come over to her house I jerk off in her feminine wash everytime and, now it's like full of cum and, last time I realized there's a huge amount of cum like it oozes out of the container and, she's uses it just fine 😉

If you like a dirty naughty story I got one for you.

last night, around 130 am and a 8 KM bike ride, yes that’s correct, that’s 1 way too lol, and add in another 2 km of bs riding around…..anyways, all day yesterday was jacking off but never came, and I thought good evening, let’s hit the streets. 

went to said location, but this time I went a little deeper into the town, where the real dirty prostitution goes on, well all kinds of things really you name it just like anywhere, it can be bad, or can be really funny, or just plain ol being a pervert and want some pussy.it was around 1245 when I got into the deeper part of the city, but let me tell you I seen some shit that almost made me wanna turn around and go home lol, but after I passed that little area, the hookers started to emerge.

the first 2 was cracked right out, just look into their eyes and they didn’t even know where they were. Hard pass for me.

the next one I seen, was from a far she started to give me that feeling, my cock was getting hard, pink pants, a fat ass, she looked about early 40s and DEFINITELY not like the first 2. I rode past her but on the other side, didn’t think anything other then I was gunna go the distance of my ride, and if anything else came up that I liked I was going to approach, and if I seen her as a last resort on the way back I’d get her.

Go up a little bit more and theirs this little blondie, maybe late 20s and looked so innconcent, couldn’t see much because of her jacket but could tell she had a sexy little body, she’s the one I wanted but stupid me I went down the wrong street and by the time I got to where she was, picked up. Figured that’s my luck sometimes but oh well. Now I was heading back up, and it was like 115 at this point.

Coming up I didn’t see anything and then from a far I seen the blonde walking away from where I seen her first, and now my dick started getting hard again.

Got closer and before I could cross into the other side of the walkway, boom, there was the pink pants chick hanging at the corner. She turns to me quicksand says hi, I said hey back in a friendly manner, literally thinking I was going to get that blonde, u til she said “ looking for a date “ ? I said ya from a little distance and said hang on.

Went down the side street and came from the back way, she was there, I was getting closer and my cock at this point was THROBBING. No hiding it, I got to her, we exchanged names, she asked me what I was looking for and I told her, I want a blowjob, but that it was going to be a bit of a different kind of blowjob, she agreed, and then I said grab my dick before we go, she grabs it and says “ wow your extremely hard “ and didn’t really take her hand away.

She then asks me “ what is this blowjob you want “ and I told her, I want to live out one fantasy of mine, and I want to do it in your mouth. Was my exact words to her.

She liked the idea, and said to me what was my fantasy, I asked her first if she liked girls, she said hell yes she was a bi sexual and loves it all.

I do confess I showed her all of my cousins, my sister, some neighbours and friends, all over 20, and I asked her which one she wanted to eat her pussy, and this was all going on while I was feeling her up, hands hard rubbing her pussy and she was rubbing my cock through my shorts, all the girls was my cousins,  I never told her the relation, she was extremely wet, she sucked my cock so hard and so fast, that when I was about to cum, she told me I couldn’t blow it in her mouth, but she jerked me off and shot the load on my phone, on my cousins face, and she buckled me, that was the greatest blowjob I ever had, I gave her my number k really hope she texts me on the weekend, I can’t stop jerking off to it now

I think the favorite slut for this weekend has been found. I still can't stop jerking off to her

Inlaws are away on holiday for a month and ive been at their place often, keeping an eye on things.

Almost every day the last week ive been using a pair of my mother in law panties and bra as a cumrag. Sit on her couch, jerk off for ages then absolutely soak them in cum. They were clean so i keep putting them back in the same place. can't wait until they get back and i have the chance to catch her wearing them

A few years back, I had an affair with my younger coworker. Hot blonde, single, career oriented, was 35 at the time. I smelled that she is one of those, who would do many things to get ahead in life, so I tested the waters with some texting. I am very into feet, so I was texting how I like her shoes, and if she could borrow me a pair, and I would get them back the next day, under a condition that she must wear them.

I took a huge risk there, but it payed off. When she took them back, she noticed the stains on the black suede. She played it cool, so, I started giving her some things, here and there, pushing her forward in the company. After a while, I would jerk off in front of her, and cum on her feet, while she was wearing shoes. She seemed indifferent, but ok with it.

Eventually, she started giving me head, and I would reciprocate from time to time, but she didn't wanna let me fuck her. The hottest part was, at least for me, that it was so obvious that she didn't enjoy it.

This lasted for over a year, until she rose far enough, not to need my backing any more, and moved to a different sector.

In today's climate, trying to repeat such a thing, with someone else, seems suicidal, so I will never do it again, but I have my memories.

Jerk for her plz

I am a long time lurker, first time confessing something.

The truth is, that I do not have too much to confess, since my sex life has been this vanilla slope, and funny enough, only thing worth mentioning, was my first gf, to whom I didn't even lose my virginity, in a way...

We were seniors in hs, so both legal, and she was this ugly girl, but with a nice body, and great, firm tits, kind of big. From the start she told me she won't have sex before marriage (even though I am old, this was an antiquated way of thinking, even back then). We would make out, she had no problem with me groping her, but only over the clothes. I would try to put her hand on my crotch, but she would back off. It drove me crazy.

One time, I was super excited, so I just said to myself, what the hell, and pulled my cock out. She didn't mind. As she was sitting on my stomach, while kissing me (she was very petite), I jerked off behind her back. She knew what I was doing, since I pressed my cock against her ass in pants, but she did nothing but kissing me, as I pleased myself.

The next step was, I would do it, and she would sit on my cock, while it is pressed against my belly, and slide up and down, until I cum. First time was really tough, since she wore some kind of jeans, but next time, she was this thing, track suit kind of thing, kind of like yoga pants, and it was better, so much so, that she came from all that dry humping.

This went on for a while, until, one time, she came from the dry humping, and I guess her body was just betraying her, so she went down, and took my, already drooling cock in her mouth, and I was done in an instant.

I never got to fuck her, but after that, things heated up, so we would usually just give each other oral. I think the most interesting part of all this was, not just that we were both virgins, hungry for sexual interaction, but the thing that she wanted me inside her, so much, that over time, we did many things just to emulate more and more sexual experiences, except the one we both wanted.

For example, this one time, I was giving her a foot massage, while she was naked on her stomach, and after a lengthy massage, my hands went up, so did I, and it ended up as me licking her ass, while rubbing her clit, until she was done, and she immediately wanted to return the favor, act per act, foot massage, going up... This thing ended up as a deed, I later found out, was colloquially called rusty trombone.

Our relationship ended, when we both went to college. We kept in touch, and were a "long distance item" for two months or so, but since neither of us was able to come visit the other, it ended in a way, that we both just stopped calling each other. Not long after that I lost my virginity to a girl in college, as most of us, at least back then, did.

Never have I ever, after this, had a more intimate relationship with another woman.

My ex-coworker. Although it's been years i don't see her, I love jerk off my cock for this woman

I fucking crave my tranny lover's cock like dr**s and I'm a fucking addict. We've come so many times together, I've lost count of the loads we've shared. I was just a 18-year-old, innocent little slut weighing 140 lbs when I met her. She popped my cherry and showed me what a real cock could do. I was always curious about sucking dick, but I was too shy to try it with a guy, so I fell hard for trannies and their thick, beautiful cocks. I saw her ad on CL and BP, so I figured she was legit. It took me a fucking month to build up the nerve to call my first escort. One night, high as a kite and horny as hell, I finally called her and got the address. I was nervous as fuck driving to the motel, but my hunger for cock overpowered any fear. I walked up to the door, and it opened automatically with her hiding behind it. My heart was pounding; I had no idea what I was in for. She revealed herself after closing the door, and holy fuck, a stallion stood before me. A 6'1 blonde Costa Rican beauty in fuck-me heels, a skimpy corset, and see-through panties hugging her thick, hard cock. I sat on the bed, trying to act cool, but my eyes were glued to that beautiful bulge. She noticed me staring, asked for the money, and I handed it over eagerly. Still sitting, she stood in front of me and told me to remove her panties. As I pulled them down, she grabbed my head and fed me that 7-inch, fat cock I'd been dreaming about. I gagged and slurped, loving every fucking second of it. I was finally the little slut I always wanted to be, hungry for her load. She stood me up, and we made out, rubbing our cocks together. It was so fucking hot. She told me to get on the bed, and I mentioned it was my first time. She looked at me and called me a dirty little slut for the way I sucked her cock. She laid me down and started spoon-fucking me from behind, slow at first to let me adjust to her thick cock. She pounded me harder and harder, stretching me out, and then made me ride her cowgirl style. I rode that majestic cock like a little twinky boy toy, loving every fucking second of it. I was getting fucked so good that I didn't want to stop. I started riding her harder, moaning like a little bitch, “FUCK THAT ASS HARDER! I'M GONNA RIDE THIS DICK UNTIL I CAN'T FUCKING MOVE! JERK ME OFF WHILE YOU FUCK ME! OH GOD, I'M GONNA CUM! DON'T YOU DARE STOP!” I blew my load, shooting cum about 3 feet in the air, and it landed all over her. She came like a horse inside me, filling me up with her hot cum. I was leaking cum everywhere, loving the feeling of being used and filled. From then on, we had so many encounters—fucking in residential homes she rented for a day or two, waiting in hotel closets while she fucked other clients so I could have her all to myself. My ultimate fantasy? To be her little fuck toy "husband," used and ab**sed whenever she wants, my ass and mouth always ready for her cock, always hungry for her load

Would you jerk to my milf mom? pm for more of her