4 Cherry Poppin on a Hand Stand

Sitting at my job watching television and I get a text message from a guy friend, I don’t remember exactly what we talked about or how it was agreed upon that we were going to have sex the day before my birthday but I do remember thinking WTF just happened?. In a few day’s I would be leaving the country I’ve know since the age of 4 to go to another country I barely ever visited and my 20th birthday was fast approaching, I was a big ball of emotion. A little back story on this guy friend: we were introduced by my one of my best friends boyfriend who thought it was a crime that I was a.) single and b.) still a virgin at the age of 19. I wasn’t completely inept at everything sexual, I had been fingered a time or two before but that’s about it. Me and said guy friend went on a few dates but nothing ever happened between us, I guess it was cause I really wasn’t interested in sex I don’t know if it was fear or just being a ditz. But I did like him (still do) and he is pretty good looking also but that's neither here nor there. So up comes the day before my birthday and that whole day I remember arguing with myself: no you are not gonna lose your virginity and hell yeah you better lose it cause you only live once and you’re going to a foreign place. In the end the latter won the fight. So he comes to pick me up and I swear I don’t remember if we talked about anything in the car but I guess we had to cause he told me we were going to a pretty nice hotel. We get to the hotel and I’m nervous as hell, not sure what to expect or even if I was really, really gonna be de-flowered by the end of the night. I do remember though that he seemed confident to me, we get in the room and it a pretty nice view of the skyline (nothing TOO fancy but nice just the same). We made small talk for a little while, made our way over to the big ass bed that took up most of the damn room. I was laying down on the bed as he got on top of me and we kissed for a while and pulls out thee biggest cot damn dick I ever seen in my life! And I blurt out “NIGGA you got a condom?” I have no idea why I said that, not like a condom was going to make his shit smaller and we both still had our clothes on.

He unbuttoned and pulls down my jeans, now I had on some cute underwear it was this pink g-string with some kind of lace shit in the front…..he liked it, he asked me to stand up so he could see my ass. He stood up behind me and rub his massive dick on my ass, being a virgin and all I knew that shit felt good :giggles: so I get back on the bed and he starts to eat me out, that was…….REALLY good, he defiantly knew how to work his tongue. I remember saying to myself this first time sex thing ain’t as bad as everyone makes it out to be. I thought to myself while he was down there if his tongue feel this good what must his dick feel like? He finish’s and ask me to give him a blow job, I was like “negro you know I don’t know shit about no dick sucking thing”. He tells me to give it a try, I figure what the hell. So I do what I THINK you’re supposed to do and lick from his nuts to the tip. And surprisingly I was like hmm, this ain’t so bad. It’s so funny cause I remember having a discussion with some of my girlfriends a few months back and we were talking about oral sex and I told them “ I don’t think I could ever do that” and here I was doing just that and enjoying it. So I experiment and try different things and what not and I he says to me “*insert real name* you sure you never did this before?” He’s making all kinds of moans and noises, so I took that to mean I was doing the damn thing…LMAO….so anyway he tells me to stop cause I guess he wanted to get to the main attraction and I was cool with that. So I lay down on the bed and he opens my legs with his hands, puts on a rubber and slowly and I mean SLOWLY enters me. And of course I tense all my muscles down there because OMG it felt so weird. He likes “You gotta relax” so I try my best but I don’t think I succeeded. I’m pretty sure he didn’t go all in, because I think I mighta died. It was painful, I don’t remember much else but I do remember the pain. It wasn’t all bad; I thought to myself maybe if it didn’t hurt so much it MIGHT be pleasurable. And one more thing I remember there was so much BLOOD, I was in the bathroom for the longest trying not to freak myself out.

But all in all, I’m glad I waited that long and I’m happy it was him to be the one that popped my cherry and gave me the best birthday present to date – sides all the pain and walking like I had something stuck up my arse and swearing my momma was gonna know/see the difference. It was good.