The Three Lucky Gentlemen

"The Three Lucky Gentlemen" refers to those three men who were given the chance to have sex with me and did. The way my blog works, if you're reading this for the first time, is I will not use these gentlemen's real names. I can go ahead and say some people will know who I am talking about anyways, despite the name changes, because all three men I consider(ed) my friends and the fact that we have many mutual friends in common. This one gets real, so be prepared for things that might gross you out or even make you think about me differently. Sorry in advance.


Let's start with Lucky #1
We will call him Drew. Drew and I were childhood neighbors. We grew up together, not necessarily as best friends or even close friends, but we grew closer our junior and senior years of high school. We hung out with mutual friends and although we went to rival high schools we never let that phase us. Most of our time spent together was with my best friend and his best friend and our favorite past time was getting high. The funny thing is that was about the only time we hung out. I remember my first time like it was yesterday...It was May 25, 2008, 20 days after my 18th birthday, and my friend invited me to a house party. I had a few girlfriends go with me and that night was full of drinking, smoking cigarettes, and smoking weed. At the end of the night everyone pretty much that didn't live at the house slept in the living room. Drew and I were on the floor and our friends were on a separate part of the floor or on the couch. The living room had seven people in all. I was really attracted to Drew and in my drunken and high state of mind I made the first move. I told him I wanted to have sex with him and he agreed. So on the floor, he put the condom on and entered me from behind and there I was losing my virginity...on the floor in a room with five other occupants. Drew stopped after about 2 minutes and said the room was spinning and pulled out and that was it. I did not have an orgasm and neither did he. We didn't even kiss. No one in the room knew it happened either, but that morning when I left the party I told my friends. I proceeded later to fall for Drew and it was the dumbest thing I could have ever done. Luckily I had his friends to remind me he did not like me like that so I could get the continued conditioning that there would be no relationship. I was crushed. I threw away my first time on the floor at a party 20 days after my 18th birthday. I mean, I 100% regret that night, but it's not like I can take it back. You live and you learn.


On to #2
Let's call him Gaston. Well after my first time failed and I graduated high school I started to hang out with this guy who hung out with some of our other mutual friends. I told him multiple times how upset I was over my first time not being the best and me not even reaching an orgasm. Well you could say this turned into like summer lovin'. I mean we spent an entire night in Cook Out's parking lot where he fingered me to an orgasm, while we listened to Senses Fail. SMH Well our first time together...my second time happened at my house in my bedroom. We turned on the TV to the one of the radio station channels, it was alternative rock I think, and then I don't know why but our foreplay was tickling and pinning each other and then one thing led to another and I experienced my first real sexual orgasm. He told me before we had sex that he wanted to show me what my first time should've been like and he did. After that night we proceeded to have sex 10 more times, mainly at my house, but also at his friend's house, his apartment, and in a hotel bathroom. The thing I regret most about this sexual experience is that after about the third time we had sex we stopped using condoms. I was stupid and thought it was okay to just use the pull out method and so did my friends. Mainly they told me I'd be okay because I was on birth control for four years before I lost my virginity. I believed them and he liked it...especially when I finished him off...yep I was that girl. He would pull out and I would swallow his load. Too much for you to handle? Sorry, I am just giving you my honest accounts on my past sexual relationships. I think that having unprotected sex was just one facet of the regret. The other part was the fact that I fell in love with him. I told him and he did not love me back. I was crushed and seriously thought we were in a relationship...I was delusional, let's be real. I was on this stupid lovesick cloud and even though my friends and family told me to leave the douchebag, I felt like I couldn't. I ended the friendship/relationship after eight months of bull shit. I deleted him off of my Facebook, I deleted his number out of my cell phone and slowly moved on. I spent several nights crying over him, but in the end this was a learning experience.


Lucky #3
We can call him Josh. Well this guy had sex with me 3 years and 3 months after Gaston...yes it took me that long to gain the ability to even be attracted to someone without letting my feelings get in the way. It also took me that long to find a guy who I considered a gentleman and someone who I thought would not disrespect me the way Gaston did in the past. Well Josh and I have many mutual friends like the other two guys, but this was probably the first time a lot of my friends that I hung out with the most did not know him. We mainly spoke to each other over Twitter and texting. I sent him several, and I mean several, scandalous text messages and before I went to see him the night we had sex I felt like that's how the majority of our conversations went. Not that I minded...but in the back of my mind that always stuck out. Anyways, so the night I gave up my celibacy I thought went very well. I hung out with Josh, his roommate and two other friends. We drank beer and later that night some smoked weed. I laughed like I hadn't laughed so hard in a very long time. I felt like I was just living in the moment carefree and really ready to have sex with Josh. The night ended with Josh and I in his room watching Auction Hunters on his bed. We were cuddling and cuddling eventually led to kissing, which led to me taking my clothes off. After this point it was time for the hanky panky...I asked him if he had a condom and he didn't. He told me we could stop there and there was a moment in my head where I said yes, that's logical, but that went out the window because it had been so long since I had had sex. I trusted him that he was clean, especially since we had been talking for about 2 months at that point in time. Well, I wasn't wet enough for him to really enter me, so he made the suggestion that I blow him to make it wet. In all honesty it was the best idea ever. I loved his penis and he proved that blow jobs don't have to suck. (no pun intended, haha!) He stopped me after a while and said it was probably wet enough and I got on top and he entered me. It felt good for what seemed to be about 2 minutes then he had to pull out...and again I did not have an orgasm. I was frustrated, but at the same time I did not think too much about it. I do wish I had had a condom for this so we both could've came at the same time because I was almost there, but that's a thing of the past. I still would like to have sex with Josh and next time actually cum, but that all depends on whether or not he wants to continue with this. We are still friends and yes I would love the benefits, but as of right now I am back at square one: masturbating...


I tell myself I am sorry for not using condoms, I tell myself I was stupid, but I also tell myself I could have stopped it. I didn't because I wanted to do it and for that I blame myself. All of these things in my mind I try to block out though because it's too late now to change the past and I just need to deal with myself at present.