I had an online sex partner for over two years. Yeah, I know how it sounds. It started on a different platform, and at first it was kind of a chat, cheeky chat if you want, and then she started sending photos, first without a face, then with, first nn, then nude, and it kind of escalated. I must admit, at that point I wasn't sure if it is not some guy sending photos, so I let it slide for a while, and then requested a cam to cam, and, bingo, no foul play there.

Now about her looks - average looking blonde, in her early 40's, never been married, single, career woman, you know the type. We started having cam sex on the weekends, and it evolved into this thing that happened almost every night. She was lonely, I was lonely as hell, so it was nice. After some time, she would turn the camera on, even when she was busy doing something, so did I, and one time, she had a friend over (I was muted and a friend had no idea I was watching). After she left, I told her that I enjoyed looking at both of them, just talking, and that I had my sexual satisfaction from viewing this.

All this span over a time period of more than a year, so things happened slowly. We had our fun with or without her present, and at some point, she told me that her friend is coming over, and that she will introduce us, me as her long distance bf, but warned me to be nice, no sexual stuff, and to keep my mouth shut, because she told her that we see each other once a month, even though we never met in person. I guess she was feeling shame for having an online fuck buddy, if that can be called that way.

So we talked cam to cam, it was fun, and that happened a few times, and in that time period, I guess she told her that we are doing cam sex and bragged about my size, and one time when we were all online, she (a friend) asked me about that, if it is true.

That night ended with me jerking off for them while they watched.

Now, fast forward almost a year, she told me that she is coming to my city, for a work thing, and if I want to finally meet her. Fuck me, I was excited as one can be, of course I would. We agreed on everything, I will come to her hotel room, and wait for her when her conference thing is over, and it will finally happen.

I was ready to leave, it was well past midnight, I just guessed she changed her mind, and is now avoiding her own room not to see me, when they entered. Later, she told me she did have second thoughts, and our mutual online friend was there, and she kept this rendez vous a secret, but confronted with doubts, after their work thing was over, she took her to a bar and came clean - how she is conflicted, how we never actually met irl, that I am waiting upstairs, and all that with a couple of drinks, so when they came in, they were both quite tipsy.

I fucked them both that night, and it was, so fucking, especially for a man with such poor sexual experience like me. We fucked all night, first round with a condom, second without, and it was beyond amazing.

This happened in September, and less than a week later, she wrote to me that this isn't healthy, and that she is breaking it off.

Now you can see my perspective, I was devastated, but I did not give up, all this time, I was trying to renew the connection, writing to her, sending her messages. Nothing, silence.

Until last night, when she came back online, responding to one of my messages. She had no time for me, but wanted to say hello, and tell me that we will talk today.

Wish me luck, I might get her back.

Why's fucking junkies so good. I finally caved a couple months ago tried a late night special and now cant stop thinking about it. At most a month goes by I cave and get another. I hate condoms so I have now cummed in three different ones. Its been a month again and im dying for it again please help!

I once got with my ex’s best friend, who was really only interested in me because my ex told her I liked to eat ass.This is a long story, in a far away time.I was living at Job Corps at the time, I was broke and fresh out of college and needed a place to stay. I entered college my junior year of high school, so I was still pretty young for a college graduate.

The ex would never let me do anal, sometimes she would let me finger it a little, but she loved having her ass eaten. After we broke up, her friend would sometimes tease me between class. Me and the ex weren’t super serious or anything, so we all pretty much stayed friends after we broke up, but by then the ex was already with another dude, so I didn’t really hang out with her much.

One day, Friend was like, “I hear you like to lick ass” and laughed, and I said, “Yeah, I do”. She was taken aback, like she expected me to deny it, I guess.
”Don’t you know that’s gay!?” she said, and I said “No, I don’t know that”, and continued on my way.

Later on she came up to me in the cafe and said, “Are you going off-res tonight?”, it was a Friday, and we were allowed to leave for weekends if you lived in the dorms. I hadn’t been planning to, but I asked, “Why?”, and she said, “You should go off-res and take me with you”.She didn’t have to ask twice, I was now planning on it. I wasn’t sure what she wanted, but I definitely had my hopes up!

Being broke at the time, most of my stuff was still with my parents, but they weren’t going to be home that weekend, which is partially why I wasn’t going home, I had no ride and I usually hated taking the bus.

But I now had a reason, and decided I’d be taking her home that weekend. I half expected her to be bluffing or messing with me, but nope, she showed up to the bus and got on with me.We didn’t talk much on the ride home, really, and I was still half-expecting a prank or for her to want something from me.

We then had to take a city bus to my house after the first bus dropped us off, and I expected her to balk or mock me, turn around and leave or something, but she just got on with me. I was at least decent enough to pay the fare for both of us, hey, two bucks, it was the least I could do. We chatted a little about nothing in particular this time, but my mind was racing a mile a minute. What did she want? Just to get off campus for a bit? Everyone knew I always had weed, maybe she just wanted to smoke?

We got home and I met a snag in my plan, because for some reason my younger sister was still there. She was supposed to have been gone, too, staying at her friend’s to go to some concert the next day or whatever.

Once she saw that I was there, and with somebody, she made it a point to be a huge pain. “What’s going on!? Why are you home!? Who is this!?”, wouldn’t leave us alone, kept asking annoying questions, kept hovering.

Friend and I were hanging out in my room and I could hear my sister hanging around outside my door, constantly walking back and forth for no reason, nosing around, it was infuriating, what would she think was going on, and why would she want to know if anything was, anyway. We were usually cool, too, so it was really bothering me that she was behaving this way.

My sister was supposed to leave that night, but she wound up staying the entire night, I’m pretty sure it was just to be annoying, just to fuck with me. I wound up staying on my couch and let Friend sleep in my bed just so my sister wouldn’t hassle us all night, not like she should have cared, it was really out of character for her, and again, infuriating. I kind of never forgave her for it, just for how uncalled for it all was. To this very day I harbor some small resentment over it, really. Gotta be honest.

I woke up the next day and took the world’s quickest shower because I was worried my sister would drive Friend crazy and I walk out to find she left or something. Eventually my sister did leave, but she dragged it on for as long as possible, just to mess with me, and again, for no reason, we were all adults, it was really odd. I was positive that Friend would be totally bothered and disgusted with me, too. If not just for my sister’s obnoxious behavior.

Once my sister left, Friend hopped in the shower and I sat on my couch seething with rage, expecting Friend to be planning her exit.

Friend came out of the bathroom in just a towel, and walked over to me.“I’ve never had my ass licked before”, she said. Well, that was unexpected. I stood up and started lowering her towel, and she let me.

Worried my sister might suddenly burst back into the house or something, I took Friend into my room, locked the door, and got her up on my bed on all fours. She had a small butt, but it was pert, and perky. Really nice, and looked especially good bent over. Perfectly pretty little butthole, too, very tight and pink.

I spread her cheeks and started eating her ass, making my way to her pussy as well, but focusing on her ass. Hey, it was why she was here!

After a while, I was good and worked up and quite ready to fuck her. I didn’t have any condoms so I had to rely on the honor system, “I’m clean, are you clean… !?”, I asked. She said yes and I was too horny to second guess her, almost as soon as she answered, I was inside her. Warm and tight, shaved, she had a nice innie pussy.

After a while she asked if I had any lube. Fortunately, I had an old bottle in my top drawer. “Yeah, I do”.
“You can fuck me in the ass”, she whispered.
Her gorgeous ass was incredibly tight and I kept having to stop so I wouldn’t cum, I was very turned on by how quickly things had escalated.
As I pulled out and stopped, clenching my gut tightly so I didn’t bust, she turned around and started stroking me. “Wait, wait, stop” I stammered, not wanting to shoot just yet.
I laid her down on her back and fucked her ass missionary for a while, I wanted to suck her big tits while I fucked her. When I was kissing her she would lightly bite and suck my lips and tongue, it turned me on even more.
Eventually I was really close and pulled out saying, “I’m really close”.
She had these big, pouty lips and she just sat up, opened them and nodded, not saying anything but moaning in agreement.
”I’m going to cum in your mouth” I said, stroking myself to climax, “I’m going to come in your mouth”.
She puckered her sexy lips waiting for my throbbing member, I kept stroking it while resting the head on her soft bottom lip, she started pursing her lips, sucking and flicking her tongue around my cock saying, “Cum in my mouth, cum in my mouth”, and I couldn’t hold back any longer, pulling back a little and repeatedly shooting thick streams all over her pretty lips and face and into her gorgeous mouth, pushing my cock between her eager lips once I was drained, my post-orgasm shaft spasming inside her mouth. She kept sucking after I came and my whole body shook with pleasure and pain.

We fell back onto the bed and just kind of laid there holding each other and breathing heavily for a while before I eventually got up to get her a towel. While wiping herself off she said, “I’ve never had my ass licked before, all my boyfriends always said it was gross or gay… “. I was going to ask if she liked it, but that felt kinda corny, so I just left it at that. This was before ass eating was a huge mainstream thing, she kept calling it “licked”, instead of eaten, but I thought that was pretty sexy.

We took a shower together, I groped and played with her luscious, wet body, soaping up her tits and ass, rubbing her up and down. Somehow she looked even better, wet, I don’t know why that’s always the case, maybe it’s just a me thing.

Afterward, we hung around watching TV for the rest of the night. We made out and groped a little, at one point she put her hand down my pants and kept fondling my nuts, but we didn’t fuck again.
Later on out of nowhere she said, “My ex was huge. Like, really big. He liked anal and it hurt. It didn’t hurt as much, with you”.
Gee, thanks, I thought, but didn’t say anything.
We chatted randomly and cuddled, before she eventually fell asleep on top of me, later on I conked out, myself.

We had a normal Sunday morning and left for the bus stop that afternoon, luckily my sister didn’t come back home at any point. At that time I would have been happy to never have seen her again, I was still so angry.
We pretty much rode both buses in silence, got back to the center and went our separate ways. I wasn’t sure if she would tell anyone and suddenly everyone would be talking or gossiping or whatever, but as far as I ever found out, she only told my ex, who Friend claimed didn’t care, and who I don’t think cared to tell anyone else, really.

But a few weeks, maybe a month later, my Ex walked up to me in the hallway and said, “Just so you know, I only ever came when I was on top”, out of nowhere, for no reason. I’m not sure if it was out of some kind of spite or revenge for finding out, or if she just felt the need to throw that at me in the moment, but all I could think to say was, “At least you came at all!”, before walking off. It didn’t bother me much, especially since during our TV talk, one of the things Friend had told me was, “I was curious, since ‘Ex’ told me you were good in bed, and that liked to lick her ass”. Hey, thanks for the good word, Ex!

Me and Friend were still cordial, but we didn’t really hang out again after that, and we (unfortunately) never hooked up again, I’m not sure if it was because of the Ex, or if she had just, gotten me out of her system, or what. All the flirting had pretty much stopped, too, and I tried to convince myself it was just a thing that happened, she got what she wanted and was done with me, guys do it all the time for instance, but I can’t deny it was a bit of blow to my ego. The little flirting thing we had was a lot of fun, I was a little sad to see it end. And I couldn’t help but thinking that perhaps she had found my sexual abilities substandard. Not like I’ve had many complaints or anything, but hey, you can’t please everybody!
Her and my ex found a new group of weirdos to hang out with, and they weren’t too fond of me and my friends, so we all kind of drifted apart, entirely. I saw Friend in passing at a rave and didn’t know it would be the last time until it turned out it was. I saw the ex one more time, the day I was leaving the program, and she ran up to me and gave me a huge hug and said a very heartfelt goodbye out of nowhere, I hugged her back and we chatted for a bit, I eventually left, and that was the last time I ever saw her.

Homemade pocket pussy I fucked with lubricant condom and lube 🤤💦

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