Often times I look back at some of the things I said or didn't do that I should have and I wish I could go back and change those things. Nothing horrible, but more insensitive. Most times without even realising it. I think that's a part of being young though and not having enough experience in such matters.

I can relate to that - I was seeing a girl, and she said she would let me fuck her. When the time came, she told me she was still a virgin. Instead of liking it, I got pissed at her because I wanted some pussy that night, and she was not ready. She told me to wait a bit, but I dumped her. What a dumb 17 year old!!

You're not alone there either.
When I think back on all the pussy and experiences that I could have had if I hadn't been either totally naive or a jealous asshole, all I can do is shake my head and laugh!

Kind of counts
 

So I’ve got a couple of things worth remembering which are more about friends who were girls than fully fledged ex girlfriends but they kind of fit the theme I think..

First one was a girl I was friends with growing up. Our parents were friends and we were pretty close but never dated or anything. She was pretty in a size zero type of way - blonde curly hair, very small breasts (32a) but nice shape and as I found out later very suckable nipples and nice legs and bum. I went away to university and we stayed friends while she was still living at home working in an office job. I met up with her during the Easter vacation for a drink and a catch up. She drove in her dads car.

During our chat she shared that she was now dating a guy from work who was slightly older (she was 19 at this point) and who she really liked and was hoping the relationship wold develop. After more chat it emerged that he wanted them to go to bed but she had so far refused. I pressed her as to why and it turned out she was embarrassed that she was still a virgin and didn’t wanrt to put him off with that because she knew he’d had other serious girlfriends in the past

After some more chat and her becoming increasingy flustered she then came out and asked if I would consider, as a friend, helping her out by taking her virginity so she had got started before she went to bed with him. She knew she could trust me as a friend and it wouldn’t mean anything in terms of her relationship with him etc etc

Needless to say at 19 I didn’t take too much persuading and I did genuinely want to help her out as a friend. We drove in her dads car to a car park I knew would be very quiet. We then got into the back seat where after much kissing I got her out of her dress and knickers and then finally fucked her very slowly and gently on the back seat of her dads car. I hadn’t thought ahead to this being a possibility and so didn’t have a condom. Therefore, it was a very careful pull out and cum on her tummy to avoid any problems later down the line.

She was a happy girl , I was happy to help her out and she went onto date the guy and eventually marry him. I very much enjoyed her wedding as she had made it clear to him that her husband had no idea how I’d helped her out :)

I guess, as some others have said in earlier posts, a more thoughtful person than the horny 19 year old i was, would have talked to her and explained that her bf almost certainly wouldn’t have minded taking her virginity for her. However, I wasn’t that person and I definitely didn’t mind getting her naked and being a good friend by casually fucking her on the back seat of her dads (who I’d known since i was a small child) car !

I satisfy my conscience that it worked out for her in the end and I hope that her bf got to enjoy loys of sex with a gf who had an ok introduction to sex..

I’ll post about my other ‘kind of ex’ experience later assuming I’m not removed from the thread for shamelessly taking advantage of my friend :)

Oh man - that list is way to long and painful to contemplate. Was such an idiot at times! :rolleyes:

Split personality
 

I dated a girl many years ago who was mostly normal, except she came from a family of Jesus freaks and was brainwashed into believing sex before marriage was evil. Often I had to work extra hard to get her naked, and even then in the middle of fucking she would have remorse and just want to stop, saying “this is wrong.” Toward the end of our relationship I talked to her about masturbating and tried to convince her it was healthy and not some kind of sin. We broke up soon after, but two or three months later I got a call one night: She said she was in bed masturbating, was super wet and wanted me to come over and fuck her. After she assured me it wasn’t a tease, I made the half-hour drive to her apartment. The door was left unlocked, so I let myself in and found her in the bedroom, as advertised in a state of bliss. I fucked her and then spent the night. Over the next year or so there were two other hookups between us. The last time I saw her we went to an adult store and bought handcuffs and engaged in some kinky action. I had lost track of her for many years, she has since married, but we connected online last summer and she was back to preaching the word and the importance of avoiding temptation, blah, blah, blah. It’s a turn on to think about the wild side of her into which I tapped two decades earlier.

My ex-wife was a trainwreck. Still is 10 years after our divorce.

But she did blow my mind at times during our marriage. I'm the one who introduced her to nudism; but she took it to a whole 'nother level.
She started out shy; wouldn't even go naked most of the time when we went to nudist resorts. Then something changed in her; probably as the result of getting to know other nudist women and feeling "appreciated" by men. One of the first "unusual" things she did was shave completely. Then she decided she wanted to stop sitting in the back of the pool area and sit out front. When she started out she would always make sure her legs were closed and no one could see her cookie. After she started shaving and lounging by the pool, she no longer kept her legs closed. She knew people could see her cookie; but she now seemed to derive some amusement from it. Mind blown.

That was just the beginning. Nudism just seemed to have liberated her. She never really got sexual with it; but she definitely had fun walking that "thin line." We had a male nudist friend whom she knew found her attractive; and my wife would flirt by pressing her boobs against him when they hugged or letting him grope her a bit. I should add that he's the only man who got a handful (and a face full) of my wife's tits and ass without getting punched in the face lol!
In that regard, I was just very proud of her. She was naked a lot; and I think pretty much everyone at the resort saw her naked from possibly every angle, because she was not squeamish about anyone seeing her with her legs wide open. Or bending over; or squatting for that matter. I knew guys were definitely having a "good look" andit only made me more proud that of all the women at the resort; it was my wife that was making heads turn.

In almost every other regard though; she was just a lazy trainwreck.

She still won't tell
 

This is in reference to frames 14 through 16 posted on this string. Tonight we were beginning to make out when my wife started talking about a girl I had screwed while we were engaged to each other. I mean this was years and years ago. So I once again in the process of looking for a defense other than "she was just a one night stand when I was horny and needed a punch. She never meant anything to me." So with that, I again brought up the night she went out with "the girls." I went into tremendous detail about how I had followed her and saw her walk into an apartment with a girlfriend of hers and two guys, with one guy leading her into the apartment with his arm around her waist. I told her I planned to let her have her lead and then barge into the party, but finally decided not to do that. I then mentioned how some guy drove her home that she was so drunk she couldn't drive, and he rushed away before I got to the door. I told her she was drunk as shit and could hardly stand up. I said that she came in the door and wrapped her arms around me and said, "I am so sorry!" Her outfit was unbuttoned to her waist. I told her to get her drunk butt in bed, and that we never talked about it. She said, "I guess I was so drunk that I don't remember it to this day. But that was a one piece outfit, and if I had to pee, I might have undone it to pee and forgotten to button it back? Did you check me out to see if I had been screwed -- maybe I had been r*p*d." I told her that I highly doubted if she had put up any fight as drunk as she was, and I had not finger checked her pussy to determine if some other guy's cum wad was filling up her cavern." She said, "Well, I could have been r*p*d, you know." I said, "If you were that drunk and got screwed, I imagine you participated at will." Then she said, "Well, I guess it could have happened, but I really can't recall that night. I do know that I recently got really drunk, and you and the guy that screwed me told me several days later that I fucked him in front of you and his wife, and I cannot remember that. So I guess it could have happened. I assure you that it wasn't planned. Back then, I didn't like other guys grabbing my ass and tits -- so it would not have been something planned." So I could only determine from that comment that she now likes for other guys to grab her tits and ass. But I already know that. I have seen her laugh and really get turned on when she has been fondled by other guys. And the guy that she fucked in front of his wife was gnawing all over her, and she was moaning and hot as hell. So we left it there. What do you think? Did she get fucked that night and remember and won't admit it or what? It seems she has selective memory.

Virtually all woman have selective memory when it comes to who they slept with unless you're real lucky, the only time uo will usually hear the truth is if you just met and she doesn't think you're interested or she expects a relationship to a one night thing or short term.

I dated this girl in college, Sandy, I dated other too, as did Sandy. I never considered her for sex because she gave off this vibe and she changed the subject if it came up. She was very attractive and had a good sense of humor so I enjoyed being with her.

One night we were at my apartment, having a few drinks and she said she wanted to ask me a personal question, "why have you never even tried to kiss me?" I explained that I was attracted to her, but I didn't think it was mutual. She just said "it is".

This lead to a make-out session and clothes slowly came off. I wasn't sure how far we were going until she said that if I didn't have a condom, she had one in her purse. I'll never forget her pussy, she was almost naturally hairless, just a few wisps of blonde hair. She was also my first experience of what I thought of as kinky. She loved to be spanked while being fingered, first girl to swallow.

We had FWB kind of relationship until she graduated and moved.