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I was always the possessive type, I didn't even like it when girls I liked and later ones that I dated had close friendships with guys. Maybe I was insecure, maybe I lacked confidence, I don't really know.
I remember when I dated my first girlfriend, let's call her Natasha. Natasha was really hot. She had amazing curves and great tits, I still think about them sometimes. Natasha had told me about her ex that she'd slept with, and I was always jealous about that. I wanted to be the only one she'd ever fucked. She was gorgeous and always got a lot of attention from other guys, which always bothered me.
We broke up after a year of dating, for unrelated reasons.
I met my current girlfriend, we'll call her Maya, a couple of years later, and we've been together for 8+ years. She's 26 and I'm 28. Maya's absolutely gorgeous, I've always been surprised on how I scored her. Maya was cute, smart, with a very girl next door vibe -- we were best friends before we finally started dating. For context, I'd always known she'd been the one from the very get go.
Maya was very different in appearance from Natasha -- petite with smaller tits, but categorically stunning legs, a great ass and having learned to my good fortune later, a really tight pussy. She'd only been in a relationship with one other guy before me, and I was the first one she'd slept with. My insecurities of course hadn't left me -- I don't know why. I've always been reasonably good looking and had never had too much trouble in getting attention from the ladies. I'd get jealous when I'd see her getting along with other guys, even when we were just friends. But these insecurities were mine to deal with, and I never let her know of this.
A little about me -- I had had my fair share of sexual experiences in between my two relationships. Slept with a couple of girls and gone to second and third base with a fair few more. Maya on the other hand, had only gone to second base with a couple of guys other than her ex, with whom she'd gone as far as third base. Just before we started dating, Maya had gone to Europe and made out with one guy and gone to second base with another -- however I didn't learn about the second escapade until much much later. When she told me about the first one, we'd already started dating and I remember feeling really upset about it -- and it stayed with me for a while. Little did I know what was set in store for me in the years to come.
A year or so into Maya and I dating, I randomly asked her about one of the guys she'd been physical with (I have no idea why -- maybe I was just curious). After a little hesitation, Maya told me. This was back when she was in college and she was at a party and got a little drunk. There was this guy, average looking she told me, who was really hitting on her. There was a moment when they were alone and he took the opportunity to kiss her -- and she kissed him back. I asked Maya -- did your tongues meet? She paused, as she's really shy, and then nodded her head. I felt my heart race -- then what happened? Maya: we made out for a while, our tongues heavily involved and he started to unbutton my shirt, I didn't stop him. He took off my shirt and undid my bra -- he gently squeezed my tits and as I didn't push him back he began playing with my nipples, he pinched them and I moaned a little when he did. His confidence grew and he put his mouth to my tits, moving from one to another and licking my chest in between. Me, heart racing like a bullet train,: How long did this go on for? Maya, ambiguously: A while. I felt this oddly intrigued and my heart was about to explode. I didn't say anything to her but I couldn't get my mind off what she said. A couple of days later, I was replaying the story in my head and letting my imagination run wild and before I knew it I was rock hard. I got myself off while imagining this story in my head. Once I was done, to my extreme surprise, I was still as excited about having heard this story -- I didn't have any post nut clarity. I found myself get off on this story multiple times in the coming years.
A couple of years later -- Maya and I were both drunk after a party and proceeded to fuck. I was on top of her and I don't know what got into me but I asked her: Can you tell me the story about the guy you kissed in Europe again. To my surprise, she didn't question me at all, but went ahead and told me the story once again. A few seconds after she was done, she said this: By the way, there's something I haven't told you. I kissed another guy at a club when I was in Europe (as I hear this, I get harder and pick up the pace of our fucking). We were making out all night and later went to the beach, where he played with my tits, licked them and explored my pussy. I'm sorry I should have told you earlier. Me: Yes you should have (only because it would have given me so much more let my mind go wild with -- but I don't tell her this).
Ofcourse, I make her tell me the second story a few more times in the coming months, usually before we're about to fuck. And to my delight, she never once asks me why I want to hear this again. I sometimes would ask myself why this turns me on so much, and I came to the conclusion that I just love the idea of my cute girl-next-door girlfriend getting in touch with her slutty side.
Another year or so later, we're fucking again (this time sober) and I'm on top (we usually start with me on top -- I get to kiss her, talk dirty and lick her tits). I don't know what gets into me -- but I suddenly go like: I know you haven't fucked anyone other than me before but don't worry, I'll let you fuck someone else before we get married (this is something I could never imagine telling her, but dick takes a man to places where he wouldn't go with a gun). And to my absolute bewilderment, she just cheekily smiles and says "okay". I had never been more turned on by anything in my life, which led to us having one of our hottest sex sessions ever.
When we were done, Maya asked me: Did you really mean that? Me exploring with another guy? Me: Yes I did, I want you to not feel held back and have all the sexual experiences that you want. It's hot for me. Maya: But what if that changes things between us? Me: The fact that I'm telling you this right after we fucked means I am absolutely sure we'll be okay after this. Also I believe in us too much for this to impact us in the long run.
I then proceeded to tell her how it was actually turn on for me to think of her with other guys and Maya being the wonderful, sexy woman that she is, didn't question me at all. In fact she even said since I'm doing this, she's okay with my fucking another woman too. I told her that for now my focus is you exploring, and we can discuss me later in the future. We had a conversation at length and decided that we would make this happen soon. I'd never been more excited in my life. It was exhilarating.
Soon, discussing her fucking other men became part of our sex routine. We were having hotter sex than ever. Ofcourse, Maya is very shy so she'd take baby steps with speaking about her fantasies. For a couple of years we went on like this, I'd ask her every now and then if she has anyone in mind but she'd always say she's not sure of whom to approach -- it would have to be someone we don't know and we were both not keen to hop onto a dating app yet. I never pushed her, just fantasising during sex was doing wonders for me. Our own sex life has always been our priority and that has always done wonders for us.
Fast forward to a couple years in the future, our sex life was hotter than ever, I still wanted her to fuck another guy (plural future me found out). She had to travel to another city for her best friend's engagement party. I was invited too, but cause of work, I couldn't make it. Maya was dressed really sexy and was having a great time. One of her best friend's friends -- tall, decent build and bearded took a liking to her, (side note: I've always been clean shaven and Maya has a thing for bearded guys). He started flirting with her and she played a long a little but let him know that she has a boyfriend. That didn't stop him though and he continued flirting with her, and Maya flirted back, encouraged by the alcohol and the attention. The tension slowly began to build up, a little touch on her back, her leaning in to say a few words in his ear.
A little while a couple more drinks later, they began dancing. A little innocent at first and then ofcourse a little more into each other. He had his arms around her waist and Maya had her's around him. He then took a leap and kissed her, it lasted for a couple seconds and then Maya gently pushed him away saying that she's not really looking to get physical (though she was really intrigued by the thought).
They were eventually in a corner of the hotel and he tried his luck and kissed her again. This time, Maya kissed him back. He grabbed her waist as they kissed passionately, their tongues getting acquainted with one another as his hands slid down to her ass and he squeezed it. They made out for a while when Maya said: this is as far as we're going tonight, he was okay with it and they kissed again, their tongues playing passionately with each other. He then slid his hand under her top and began playing with her tits, Maya didn't push him back -- she was really into it. He pinched her nipples and made her moan. She grabbed his dick from over his jeans and found that he was hard. They pulled away after that.
The bar was closed at that point, so he asked her if she wanted to come to his room for a drink. Maya: yes, but we're not having sex. That's fine, squeezing her ass playfully, I just wanna explore your tits and maybe play a little with what's between your legs. Maya, turned on by that, just smiled in a nonchalant way, not trusting herself to speak.
They get to her room and before they could take a few sips of their drinks, begin making out again. He doesn't hold back and begins playing with her tits immediately. A minute or so after he takes her top off and begins licking and gently biting her nipples. He was going to town. Maya was loving it and let him go on, taking his shirt off in the process. Before they knew in it, they were both in their underwear on the bed.
He then slides his hand into her underwear and begins exploring her pussy, which is amazingly tight. With his hands playing her with clit, and his mouth on her tits, Maya goes crazy. She takes his underwear off and begins stroking his dick -- he was a little bigger than me (I'm about 6 inches and he was maybe 7) which Maya loves. She's always wanted a bigger dick, and I've always wanted that for her. She strokes him and they stay that way for a while, playing with each other's pussy and dick. Unfortunately, Maya didn't blow him that night.
A little while later, Maya: We're still not fucking tonight (though at this point she's not entirely sure of herself), he just nods in agreement and begins playing with her pussy again. Maybe about five mins later whispers in her ear: wanna fuck? Maya, overcome by her desires, nods, but says: get a condom. He finds one, slides it on and begins fucking her from top, licking her tits and pounding her hard. He doesn't last very long and finishes in maybe another five mins.
And then comes session two, this time Maya takes control and says I'm going to be on top. She rides him like a dirty slut and then they switch to reverse cowgirl. He then flips her on her back, smacks her ass, and begins pounding her from top again. He asks if he can take the condom off, to which Maya says: No but I'll let you come on my tits this time. And that's exactly how session two ends, with him finishing on her tits.
Final, and last session of the night, it was dawn outside -- they were making out again and she was stroking his dick. I'm out of condoms he said. Maya pauses, and then: okay but you have to pull out, to which he nods. And she loved taking him raw, it was the best session of the night and they fucked for the next 15-20 mins like that, switching between missionary, cowgirl, and reverse cowgirl (Maya didn't let him fuck her doggy sadly as she knew that was my favourite position -- I wish she had though). He finished on her tits again and they kissed goodnight before Maya left for her room.
A couple of days later, Maya came back home, and told me all of it. She was feeling incredibly guilty and thought I may not forgive her. But as she told me, I found myself get aroused like I've never been before in my life, like this animalistic feeling grew inside me making me go wild. We immediately fucked right after, without me hearing too many of the details. After we were done, I consoled her and told her I was absolutely fine with this and it hasn't changed anything between us. She felt reassured and relieved. An hour later, I asked to tell me the whole story again but leave out a few dirty details (to save for our future session). But this I wanted her to tell me what happened while she stroked me. I came harder than I ever had.
Over the next few days, we fucked like monkeys, with having her a reveal another dirty little detail each time it happened. I realised I wanted her to do this again, and let her know. She was onboard, provided it happened organically and that we don't actively search for this. I was on the same page. It's been a year and a half since her first experience and she's fucked two more guys since then. I can't wait to share the details of this here with you guys.
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