(M)y hottest experiences with a long term (F)riend

So this is the hottest two experiences of my young 24 years of life and the funny part is that neither even end with actual sex so if you're here for spank material you'll be disappointed. A little background before I begin.I am probably what you would call an average looking male… 5'9" bout 140lbs.. no 6 pack abs or ripped muscles but also not pudgy.. just kind of average skinny I guess. As far as I know there's nothing too distingishing about my appearance. And my dick is on the higher side of average measuring in at just over 6.5". I have always been a very sexual person even when I was little. My first experiences were the basic playing doctor with a female friend and from then on I was hooked, maybe even to the point of sexual addiction if you believe in that sort of thing. And that brings with it a lot of various kinks or fantasies that to this point have only been touched on briefly as the sort of girls I usually get with are the ones who are into very vanilla sex although I do have a few good stories I could share if this gets some good response.

Anyway so this story involves a girl whom I met my junior year of high school. I'll call her Sally, again not her real name. She is about my height and had shoulderish length brown hair.. its way longer now and looks even hotter. Very pretty face with really pretty eyes and a smile that leaves you breathless. She has nice C-cup? sized breasts.. I've never been good at determining size but they were nice without being too big.. and an a nice round butt that I would always stare at as she would walk away. I always thought of her as very pretty and was very intimidated by her as she was beautiful and confident and I was neither of those things. We sort of had an on and off relationship where we would hang out and I would build the courage to finally ask her out but by that time she was always with another guy which also completely wrecked my confidence. She later said that she was never sure if I was actually into her because I would never make a move. Our relationship during that time was very flirty but never made a move to kiss her or take the relationship further. Eventually we both stopped talking and I found myself with a girl who both made me become more confident and also completely destroyed my confidence multiple times… but hey we all need to experience that kind of relationship at least once right? And she found a guy and got engaged.

The first experience that I will tell was around 2 years after the initial falling out that we had. One day out of the blue Sally texted me after not having heard from her in probably more than a year. She asked if I wanted to hang out and of course I said yes not thinking it would be anything more than driving around and catching up. She came over and asked if I wanted to go for a drive which is what I expected. What I didnt expect was that she was taking me to a local beach. We didn't swim and there was no stripping down or anything.. infact there still wasn't any physical contact or kissing, yes I am a pussy I know. But the whole time we we laid on the beach and talked about everything in life and she would talk and I would listen and just look at her just taking in the beauty of the moment. I had made a comment that it was so nice out and we should go for a swim but Sally shot that down saying that she didn't think people would enjoy seeing her in a thong. I then made a comment that I would love to see her thong and Sally laughed at that… even though I was serious and just thinking about it was enough to make me hard. Anyways the rest of the day was perfect we connected just like nothing had ever changed. After she took me home I thought about how perfect the day was and texted her telling her all this and after that our texting relationship became a whole lot different. We would not only talk about life but also sex quite a bit. I discovered that she was also very sexual and the first time she texted me that she was masturbating to the thought of me made me just about blow my load right there while I was at work.

Fast forward a few more years. I am in an on again off again relationship for about 3 years. Things go well for a little bit and then it just hits rock bottom with my current gf and then things would eventually get better. The current gf and I have lots of sex during the good parts that usually lasts a few months before things go bad for one reason or another and then we break.. do our own thing for awhile before coming back together and fucking like rabbits again. During this same time Sally moves away and gets a serious bf and had a baby. Sally and I would talk during this time off and on as well. Mostly discussing life and how we both have feelings for each other but she can't move from her current situation and neither can I. Finally after about 3 years we finally get a chance to meet up as shes home visiting family.

I drove from my place to her mothers place about an hour and a half away. We spent the first couple hours watching her daughter watch Frozen and just talking. It was really sweet to finally get to see her and meet her daughter and everything and the whole time I was admiring how beautiful Sally still is. After awhile we get Sally's grandma to watch her daughter and we go to Sally's room where we spend more time talking and catching up… All I wanted to do was kiss her and just let all my emotions out but I never do.. Until Sally tells me that she wants to lay down. We lay down together and within seconds we are full on making out. HOLY SHIT! You ever have a moment where it's like every ounce of emotion and passion just comes gushing out of you? This was that moment for me. Finally after 7+ years of wanting this moment I finally got it and it was amazing. We made out for a long time as our tongues pushed together. Eventually I got the nerve to start kissing her ears and her neck and kiss down her body right to her waist.. and then she said not so fast.. So of course I obliged and kissed my way back up her body. We made out some more.. her kissing my neck and grabbing my back and me kissing her neck and grabbing her back and her ass when all of a sudden she starts rubbing my extremely hard cock through my jeans. I mean I don't think I'd ever been this hard in my life and so I took that as my cue to start rubbing her pussy over her pants. We continued our making out like teenagers and aggressively rubbing each other for awhile when she undid my jeans and starting stroking mycock. I have no clue how I didn't bust right there but I didn't. I let her continue the handjob for awhile before I slid my hand in her pants and starting playing with her clit. SHE WAS SOAKED. Having been shot down already from ripping her pants off and going down on her earlier it took all my strength to hold back but I did slid a finger in her tight pussy. I proceeded to finger her as she got wetter and tighter around my finger as she came. Every sexual fantasy I've had about Sally had me so curious how she tasted so I slid my finger out of her and brought it to my mouth so I could just taste her sweetness. Apparently she also like the way she tastes because she sucked on my finger after I did as I was telling her how good she tastes and how I want to go down on her. This must have excited Sally because she pushed me back on the bed pulled down my pants and put my cock in her mouth. She gave me some mind blowing head for a couple minutes. Sally definitely knew what she was doing and it felt amazing. Unfortunately thats the same time her daughter starting being fussy and she we stopped and she went to go put her daughter down for bed. I laid there debating if I should stay and see what happens or get up and go since I had to be at an interview at 7 in the morning and it was already late and I still had the drive home. Soooo I chose the logical but wrong decision.. and got up to leave. We made out a little more before I left and that was that. Although the whole drive home we texted about what happened and how we both felt about it. We felt the same way that it was amazing and should not have waited so long to finally kiss. And that when she got up to put her daughter to bed that she was going to come back and fuck me… FUCK! wrong decision to leave. The rest of the trip home we discussed sex and how she was watching porn and we were both super horny and needing more. Part of me is ok that I left because it leaves that little bit of sexual tension and mystery still there but part of me still wishes I hadn't left.

The next few months were spent talking all day every day. A lot about life and how we should be together and I was actively looking for a job where she lives. And a lot of sexting including the only times where I sent snaps of my jerking off to the thought of her… which apparently gets her off too. Then after a few months of this I made an even bigger mistake of falling into a depression of sorts and had all these thoughts of what if I move there and she gets back with her ex (baby's father) and what not. Got scared and started to ignore her. We talked a little bit after that but now she ignores me and is back with her ex while I am sort of just rooming my ex. No sex.. little hanging out like we are dating but nothing official and I can't stop thinking about Sally and how everything was going perfect until I messed up.

Sorry this is so long… and theres not a lot of hot jerk off material or anything like that. I just needed to vent and get this off my chest I guess.

Source: reddit.com/r/gonewildstories/comments/3auv54/my_hottest_experiences_with_a_long_term_friend