26/10/2016
To start this story the right way I should start by saying that I've been with my girlfriend for 6 years, we call each other boyfriend/girlfriend but it's basically a marriage. We moved together two years ago since we've always been great together and we understand each other perfectly. We met when she was 18 and I was 19. I was her first boyfriend ever, her first kiss and the guy she lost her virginity with. She's always been a shy girl and she's never been the kind who dresses provocatively even tho I have never restricted from dressing or wearing whatever she'd like. I've never been a jealous boyfriend and I can say that I have always been very comprehensive as well.
By the time she started college things started to get a little complicated since she was starting to leave that little girl behind and starting to get into adulthood, plus everyone changes in college (lol). One of her friends who was a little slutty was always asking her if she was never curious about finding out how being with another man would be and always putting ideas in her head. She always told me everything and her answer to that was that she loves me and she didn't need to be with another man. I was happy with that because I can say I love her too and I don't want to lose her.
For a while we were having that type of conversation because even when she wasn't that type of girl her friend was kinda right. I had sex with other girls before her so I can say I had other experiences but she never had any before me. We always talked about it because I didn't want her youth to be over and never done anything stupid or explore her sexuality, and I'm not even talking about her being with another man, I'm talking about that she was always so reserved, we never did anything sexual in the car or in a park or anything we could have remembered as a crazy experience. I fell in love with her for the person she is so I didn't want to push it too hard either I really didn't mind that she was that way but at the same time I was always letting her know that I was okay with exploring and being a little more open sexually.
In march this year (2016) we decided to take a short vacation to Puerto Rico for a week. Our plans were pretty much just relax and enjoy from that beautiful island in the Caribbean. There were when things started to change a lot. Surprisingly for me the second day there she decided to walk around San Juan in very short shorts which woahhh she looked amazing (since she has a really nice body). She never ever wore anything like it before, that same day we got inside a store and she saw this very sexy and provocative dress that was definitely not her type but she fell in love with it and she bought it. At night we were getting ready to go out to a club get some drinks and she almost didn't wear that dress since it was unlike her. She was looking so hot in it and it was like nothing she ever wore before. When we got to the club we had some drinks as planned and a lot of guys were checking her out, she was blushing all the time and she confessed me that one of the guys checking her out was cute. I told her to go for it and flirt with the guy who was with one of his friends. I never thought she would go for it but she did, I'm not sure if it was the alcohol or just the fact that we were in another country and she was feeling different. She went flirted with the guy and started to dance with him and with his friend, I was sooo surprised but at the same time I just wanted to let her enjoy and be free. I saw while dancing there was touching and then kissing, they went to sit after dancing and they were making out and if you think that was the most shocking part then imagine the other guy's friend there kissing her and touching her as well. I saw it was getting pretty wild so I went there and just acting like I was just a friend I gave her the car keys so they could go to the car I wasn't sure how far she was going to go with all that. I stayed close to the car just in case but far enough that they couldn't see me. After a while she sent me a text to take her back to the hotel room. I thought they were done whatever they were doing and I was just excited to hear what she thought about that experience. When I got to the car they three were still there, she was totally naked and both guys had their pants down. As soon as I got in the car she told me they knew I was her boyfriend and if it was okay to go to the hotel room with them. I said yea and I won't lie, I would've rather be with two other girls than two other guys but what the hell this is a new experience she seemed to be enjoying it and it kinda turned me on. On the way to the hotel room I could see that she was giving head to both guys and they where playing with her all the time. In the hotel parking she didn't want to put her dress back I guessed she was so horny that she wasn't thinking clearly anymore, she got out of the car totally naked but I gave her my shirt. In the elevator going to the 9th floor there was other couple right there with us but they didn't stop, they couldn't take their hands off each other and the other couple didn't really cared much either, they were pretty much just enjoying of the two guys playing with my girlfriend who didn't have any underwear and they could see how they guys were fingering her. When we got out of the elevator the other couple whose today are our friends and we keep communication are from Boston, she's 24 and he's 26. They asked us if we didn't mind them to keep looking at all that. I wasn't sure what to say but my girlfriend said it was okay. At that moment I didn't know what was going on anymore. Finally we got to the room and for the first time ever my girlfriend had sex with two other guys the same day! We all took turns on her and I can tell you she was enjoying it so much, moaning and having multiple orgasms ( I know that because she told me after) They other couple obviously got really turned on and they had sex as well but we didn't interact with them at that time. After all that sex we had the couple left and they gave us their numbers. The other two guys fell asleep with us that night. In the morning my girlfriend and I were the first ones to get up and while we were in the bathroom she was telling me how she couldn't believe what just happened and that it was so crazy, I asked her if she would do it again while she was putting her clothes back on and at the same time I started to take her clothes off. She surprised asked me what was I doing and I took her back to the room and told her why doesn't she wake them up giving them head. She smiled and went right to them and did it, the guys woke up really happy and we fucked her again, we all came on her body and after that they guys left the hotel room we got in the showered and laugh about all the craziness of that night and morning. More happened the rest of the vacations but I want to wait for you guys to let me know if want me to write about the rest of the vacations.