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- Jun 16, 2013
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The way I lost my virginity was a pretty funny story and I'm going to share in hopes of two things:
1. It makes you laugh
2. You have a good story to add from when you popped your cherry
Caveat: long read but I think it's worth the investment in entertainment.
It was the day after I graduated high school (late bloomer here) and a day before I was leaving to Nicaragua on a surf trip. Back then I was a total donkey loser and participated in numerous illegal activities and used to be an entrepreneur of sorts.. anyway you get the picture. And I was at a new customers house that I knew via social circle. The customer was a girl and she was getting stuff for her and her boyfriend. She seemed fairly flirty whenever I talked to her and she was texting me randomly just to "chat" which I wasn't really into.
One day she asked to meet up and smoke a doob with her in which I was riding around anyway and figured why not. In the car ride she went total apeshit and started telling me her life story and how she cheats on her boyfriend because he's a loser and stays with him because she has no where to live. She then told me how she looking for a fuck buddy right now. And she told me all this without zero prompting or deep diving whatsoever and it kind of freaked me out, especially since I had just smoked a doob and she's dropping this on me.
In retrospect that probably would've been the proper time to escalate to car sex but I was a little timid and the idea of sex made me nervous. But she literally just exploded into this rant and I was overwhelmed so I dropped her ass off, in order to give myself time to digest this new information.
New info digested was there is a girl that seemingly wants to have sex with me, though not hot (had tits, not prettiest face, no ass whatsoever, on the scale probably a 4-5, though at the time I rationalized her to be at least a 6.5), but a chance to lose my virginity!
About a week later I had settled down and regained my composure. I called her and said we need to hang out to celebrate my graduation in which she obliges and I go to pick her up.
I had just finished listening to this new Z-ro album I got and he was rapping about fucking some dudes baby momma doggystyle while she rolled up blunts to smoke in a motel... I of course was inspired to be like z-ro! Minus the baby momma part.
So I formed a plan.
You see I had no idea how to escalate or talk about sex or anything I was totally clueless. So I figured when she asked what we were doing I was just going to tell her we're going to hang out and smoke in a motel, wink wink.
Anyway I picked her up and when she asked what we were doing I told her exactly that. She didn't really seem to get the hint and quickly forgot when I changed the subject (I figured she'd be less likely to reject my advances if I could just get the room paid for before she realized what was happening.. what a dick right?). I drove to the nearest motel in my city and told her to hang while I took care of stuff. Oh yeah she brought her fucking dog with her so she went to let her dog piss on the building while I went inside. Beautiful I know.
Turns out the motel costs 80$ and I was like "WTF!". I had money back then don't get me wrong but I was not paying no 80$ for a room for an hour no sir!
So I headed into the city 15 minutes away. I check the motels downtown to see how much they were and they were all $80 as well. I'm thinking "FUCK if I don't get a room quick she's going to realize I'm shopping for motel rooms so we can shagg it up! I need to hurry before she realizes!".
At this point I'm like fuck it I know there's cheap motels in the hood so I'll just find a super ghetto motel that will be cheap enough for me to actually want to pay.
So we begin our journey to the ghetto of Pensacola, Florida. Aka Alphabet City (named for the street names A st. - Z st.). She now realizes that I'm driving into the hood and asks "So what are we doing again?" very inquisitively/bitchy. I still can't believe she hasn't caught on to what I'm doing at this point so I tell her the truth: "Well the other week you were talking about how you just want a fuck buddy sooooo... let's fuck buddy
. " Probably the boldest/corniest thing I've ever said to a woman at that point in my life. And though she didn't look highly excited she didn't seem totally distraught and didn't object. "IM IN!" I think.
I go find the closest motel I can find, once in the hood, and if memory serves me correct it was the "Budget Inn". Really nice place it had parking spots, not too many loiters selling drugs on the side of the building, and these dim lights that almost represented street lights to light the parking lot for safety (at least they tried). Also a really nice front view of another beat down motel across the street and on the other side of the street was the projects. So yeah you can imagine how warm and friendly everyone was.
So I go up to the pay window and try and talk the price of 45$ down to 15$ and fail miserably (think it had something to do with my nice clothes, white skin, and suburban accent). I get the key and we enter the room. "OMG this is acutally happening!".
I sit down on the bed and she follows I'm not in a hurry and decide to procrastinate as much as I can before doing the dirty deed. I roll a blunt of chronic and we talk. Oh yeah she still had her fucking dog with us in the room jumping everywhere and being a general nuisance. I told her to leave it in the car but she didn't want someone to break into the car and steal her dog.
So we go outside and post up on the street corner across the street from the projects to smoke our blunt and it's night time. Maybe not the best idea I've ever had but I don't think we looked like completely outsiders. We both looked like broke hood rats for the most part. Two big black guys walked down the street and mean mugged us for what I'm guessing they were jealous we were smoking good weed in the middle of the street. Though they probably were both strapped and ready to bust on any mort giving them an eye they didn't appear overly aggressive.
So we survived smoking a blunt on the corner of the street and I knew it was time to head back inside to do the dirty... a mixture of complete dread and excitement all amplified by the THC currently traveling through my body causing me to overthink everything even more.
We get back in the room and I continue to procrastinate by small talk and eventually the thread dies out completely and were looking at each other in complete awkwardness. I feel like at this point I should be doing something to initiate escalation (touching/kissing) but I have no idea how and I'm too scared and literally am a deer in the headlights... in complete awkward silence *Facepalm*
Anyway she looks down, gets up from the bed, sighs, and starts taking her clothes off to where she's in a bra and boyshorts. I'm standing in utter amazement with my jaw open. She undoes her bra and is now topless. The first real pair of titties I've seen in broadday light. And it's fucking awesome! Not only does she do that but then she sees I'm still not touching/caressing her and she sighs again and takes off her boyshorts and lies on the bed completely naked and I'm in my jeans and t-shirt just watching in amazement.
I realize I'm still clothed and rip my clothes off my body in a panic and then tentatively walk over and start fingering her.
At this point I'm still trying to play it off like I know my way around the bedroom so I stupidly ask her if she's the kissing type or not and she gives me the "WTF" look.
I say this because I don't want to kiss her so I'm hoping she'll say she not the kissing type. Turns out she is the kissing type (imagine that) so I tell her I'm not and continue to finger her until she seems wet enough to enter. You can imagine how passionate we are. Quite a romantic evening so far aye?
I go to throw a condom on and she says she's allergic to latex. I call her out and she says that I can fuck her with a condom on but she'll get an allergic reaction and break out in hives. Way to completely kill the vibe :/.
At this point I'm saying fuck this is happening! It's too late to turn back now! I mount her tentatively and freaking miss trying to put my dick in her in missionary. Wow, so much for keeping up appearance of pretending to know my way around the bedroom. With help from her I finally get my cock inside her and we start fucking. I'm so blown away of how easy and not big of a deal this is and I start enjoying it.. a lot!
To make a long story short I finally get my penis inside her and we shag for a good 60 seconds before I feel the urge to splurge and pull out and cum all over her belly. . It was an amazing 60 seconds to say the least and after I finish she looks at me and gives me the "WTF" look again. I go fetch her a towel to clean herself up with.
We shagged again for an hour this time and then left to return back to the suburbs. Mission successful!
It was the most emotionless passionless shitty sex ever.. well maybe not my friends that are girls seem to complain more.. but for a Casanova in training it was pretty fucking bad I give myself a D- for that night.
So yeah my epic story of losing my virginity. Hope someone got a laugh out of it.
Oh yeah I almost forgot to mention. Literally two days later I drank way too much alcohol and ended up fucking my stomach up really bad and giving myself ulcers. I had always drunken that much before in the past and it never hurt me but it did this time. I was in so much pain I had to stop drinking altogether and the pain lasted for a good 6 months. After about the 3rd months I had completely convinced myself that I had an STD that was giving me the stomach pain (from not wearing a condom). I was very anxiety ridden and thought I literally got an STD from losing my virginity I was beyond pissed.
When I finally went to the doctors, after 5 months of anxiety and self pity, they told me I simply had stomach ulcers and needed to take medicine for a little while...
So much for being as cool as Z-ro
Well that's my story of my first shagg and hopefully someone found it entertaining. I had fun reliving the experience as I wrote it, besides thinking I had gotten an STD but aside from that!
Hope to hear your misadventure...
-Rob
1. It makes you laugh
2. You have a good story to add from when you popped your cherry
Caveat: long read but I think it's worth the investment in entertainment.
It was the day after I graduated high school (late bloomer here) and a day before I was leaving to Nicaragua on a surf trip. Back then I was a total donkey loser and participated in numerous illegal activities and used to be an entrepreneur of sorts.. anyway you get the picture. And I was at a new customers house that I knew via social circle. The customer was a girl and she was getting stuff for her and her boyfriend. She seemed fairly flirty whenever I talked to her and she was texting me randomly just to "chat" which I wasn't really into.
One day she asked to meet up and smoke a doob with her in which I was riding around anyway and figured why not. In the car ride she went total apeshit and started telling me her life story and how she cheats on her boyfriend because he's a loser and stays with him because she has no where to live. She then told me how she looking for a fuck buddy right now. And she told me all this without zero prompting or deep diving whatsoever and it kind of freaked me out, especially since I had just smoked a doob and she's dropping this on me.
In retrospect that probably would've been the proper time to escalate to car sex but I was a little timid and the idea of sex made me nervous. But she literally just exploded into this rant and I was overwhelmed so I dropped her ass off, in order to give myself time to digest this new information.
New info digested was there is a girl that seemingly wants to have sex with me, though not hot (had tits, not prettiest face, no ass whatsoever, on the scale probably a 4-5, though at the time I rationalized her to be at least a 6.5), but a chance to lose my virginity!
About a week later I had settled down and regained my composure. I called her and said we need to hang out to celebrate my graduation in which she obliges and I go to pick her up.
I had just finished listening to this new Z-ro album I got and he was rapping about fucking some dudes baby momma doggystyle while she rolled up blunts to smoke in a motel... I of course was inspired to be like z-ro! Minus the baby momma part.
So I formed a plan.
You see I had no idea how to escalate or talk about sex or anything I was totally clueless. So I figured when she asked what we were doing I was just going to tell her we're going to hang out and smoke in a motel, wink wink.
Anyway I picked her up and when she asked what we were doing I told her exactly that. She didn't really seem to get the hint and quickly forgot when I changed the subject (I figured she'd be less likely to reject my advances if I could just get the room paid for before she realized what was happening.. what a dick right?). I drove to the nearest motel in my city and told her to hang while I took care of stuff. Oh yeah she brought her fucking dog with her so she went to let her dog piss on the building while I went inside. Beautiful I know.
Turns out the motel costs 80$ and I was like "WTF!". I had money back then don't get me wrong but I was not paying no 80$ for a room for an hour no sir!
So I headed into the city 15 minutes away. I check the motels downtown to see how much they were and they were all $80 as well. I'm thinking "FUCK if I don't get a room quick she's going to realize I'm shopping for motel rooms so we can shagg it up! I need to hurry before she realizes!".
At this point I'm like fuck it I know there's cheap motels in the hood so I'll just find a super ghetto motel that will be cheap enough for me to actually want to pay.
So we begin our journey to the ghetto of Pensacola, Florida. Aka Alphabet City (named for the street names A st. - Z st.). She now realizes that I'm driving into the hood and asks "So what are we doing again?" very inquisitively/bitchy. I still can't believe she hasn't caught on to what I'm doing at this point so I tell her the truth: "Well the other week you were talking about how you just want a fuck buddy sooooo... let's fuck buddy
. " Probably the boldest/corniest thing I've ever said to a woman at that point in my life. And though she didn't look highly excited she didn't seem totally distraught and didn't object. "IM IN!" I think.I go find the closest motel I can find, once in the hood, and if memory serves me correct it was the "Budget Inn". Really nice place it had parking spots, not too many loiters selling drugs on the side of the building, and these dim lights that almost represented street lights to light the parking lot for safety (at least they tried). Also a really nice front view of another beat down motel across the street and on the other side of the street was the projects. So yeah you can imagine how warm and friendly everyone was.
So I go up to the pay window and try and talk the price of 45$ down to 15$ and fail miserably (think it had something to do with my nice clothes, white skin, and suburban accent). I get the key and we enter the room. "OMG this is acutally happening!".
I sit down on the bed and she follows I'm not in a hurry and decide to procrastinate as much as I can before doing the dirty deed. I roll a blunt of chronic and we talk. Oh yeah she still had her fucking dog with us in the room jumping everywhere and being a general nuisance. I told her to leave it in the car but she didn't want someone to break into the car and steal her dog.
So we go outside and post up on the street corner across the street from the projects to smoke our blunt and it's night time. Maybe not the best idea I've ever had but I don't think we looked like completely outsiders. We both looked like broke hood rats for the most part. Two big black guys walked down the street and mean mugged us for what I'm guessing they were jealous we were smoking good weed in the middle of the street. Though they probably were both strapped and ready to bust on any mort giving them an eye they didn't appear overly aggressive.
So we survived smoking a blunt on the corner of the street and I knew it was time to head back inside to do the dirty... a mixture of complete dread and excitement all amplified by the THC currently traveling through my body causing me to overthink everything even more.
We get back in the room and I continue to procrastinate by small talk and eventually the thread dies out completely and were looking at each other in complete awkwardness. I feel like at this point I should be doing something to initiate escalation (touching/kissing) but I have no idea how and I'm too scared and literally am a deer in the headlights... in complete awkward silence *Facepalm*
Anyway she looks down, gets up from the bed, sighs, and starts taking her clothes off to where she's in a bra and boyshorts. I'm standing in utter amazement with my jaw open. She undoes her bra and is now topless. The first real pair of titties I've seen in broadday light. And it's fucking awesome! Not only does she do that but then she sees I'm still not touching/caressing her and she sighs again and takes off her boyshorts and lies on the bed completely naked and I'm in my jeans and t-shirt just watching in amazement.
I realize I'm still clothed and rip my clothes off my body in a panic and then tentatively walk over and start fingering her.
At this point I'm still trying to play it off like I know my way around the bedroom so I stupidly ask her if she's the kissing type or not and she gives me the "WTF" look.
I say this because I don't want to kiss her so I'm hoping she'll say she not the kissing type. Turns out she is the kissing type (imagine that) so I tell her I'm not and continue to finger her until she seems wet enough to enter. You can imagine how passionate we are. Quite a romantic evening so far aye?
I go to throw a condom on and she says she's allergic to latex. I call her out and she says that I can fuck her with a condom on but she'll get an allergic reaction and break out in hives. Way to completely kill the vibe :/.
At this point I'm saying fuck this is happening! It's too late to turn back now! I mount her tentatively and freaking miss trying to put my dick in her in missionary. Wow, so much for keeping up appearance of pretending to know my way around the bedroom. With help from her I finally get my cock inside her and we start fucking. I'm so blown away of how easy and not big of a deal this is and I start enjoying it.. a lot!
To make a long story short I finally get my penis inside her and we shag for a good 60 seconds before I feel the urge to splurge and pull out and cum all over her belly. . It was an amazing 60 seconds to say the least and after I finish she looks at me and gives me the "WTF" look again. I go fetch her a towel to clean herself up with.
We shagged again for an hour this time and then left to return back to the suburbs. Mission successful!
It was the most emotionless passionless shitty sex ever.. well maybe not my friends that are girls seem to complain more.. but for a Casanova in training it was pretty fucking bad I give myself a D- for that night.
So yeah my epic story of losing my virginity. Hope someone got a laugh out of it.
Oh yeah I almost forgot to mention. Literally two days later I drank way too much alcohol and ended up fucking my stomach up really bad and giving myself ulcers. I had always drunken that much before in the past and it never hurt me but it did this time. I was in so much pain I had to stop drinking altogether and the pain lasted for a good 6 months. After about the 3rd months I had completely convinced myself that I had an STD that was giving me the stomach pain (from not wearing a condom). I was very anxiety ridden and thought I literally got an STD from losing my virginity I was beyond pissed.
When I finally went to the doctors, after 5 months of anxiety and self pity, they told me I simply had stomach ulcers and needed to take medicine for a little while...
So much for being as cool as Z-ro
Well that's my story of my first shagg and hopefully someone found it entertaining. I had fun reliving the experience as I wrote it, besides thinking I had gotten an STD but aside from that!
Hope to hear your misadventure...
-Rob
